螺“4.4”壬烷-1，6-二醇的不对称合成研究
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摘要
具有螺环C2对称轴的手性化合物在不对称合成领域起着非常重要的作用,螺[4.4]壬烷-1,6-二醇就是这些手性配体中的一种,它们的结构特点是分子中有三个连续的手性中心,其中一个是刚性的螺季碳,两个手性的羟基可以很方便地进行衍生化。
本论文主要包括以下三方面的内容：一,介绍了螺[4.4]壬烷-1,6-二醇的研究背景；二,介绍了其它具有Q对称轴的手性化合物和它们在不对称合成中的应用；三,基于我们组内发展的半片呐醇重排反应,我们用手性布朗斯特酸促进环氧醇手性开环,再通过还原的方法得到不同立体构型的手性螺[4.4]壬烷-1,6-二醇,这为我们进一步研究此类化合物在不对称合成中的作用奠定了良好的基础。
Compounds with the C2 symmetry axis play a very important role in the field of the asymmetric synthesis and the spiro[4.4]nonane-1,6-diols belong to this kind of ligands. The compounds are structurally characterized by three consecutive chiral centers, one of which is rigid spiro quaternary carbon, and two hydroxys can be easily derivatized. The contents of this thesis mainly include:
1. The introduction of the research background of spiro[4.4]nonane-1,6-diols;
2. The introduction of other chiral compounds with a C2 symmetry axis and their applications in asymmetric synthesis;
3. Based on the development of the semipinacol rearrangement in our group, we used chiral Brφnsted acid to promote a ring opening of the epoxy alcohol and reduced the products to obtain the chiral spiro[4.4]nonane-1,6-diols with three different stereochemistrys. This provides us a good foundation for further developing these compounds in asymmetric synthesis.
本论文主要包括以下三方面的内容：一,介绍了螺[4.4]壬烷-1,6-二醇的研究背景；二,介绍了其它具有Q对称轴的手性化合物和它们在不对称合成中的应用；三,基于我们组内发展的半片呐醇重排反应,我们用手性布朗斯特酸促进环氧醇手性开环,再通过还原的方法得到不同立体构型的手性螺[4.4]壬烷-1,6-二醇,这为我们进一步研究此类化合物在不对称合成中的作用奠定了良好的基础。
Compounds with the C2 symmetry axis play a very important role in the field of the asymmetric synthesis and the spiro[4.4]nonane-1,6-diols belong to this kind of ligands. The compounds are structurally characterized by three consecutive chiral centers, one of which is rigid spiro quaternary carbon, and two hydroxys can be easily derivatized. The contents of this thesis mainly include:
1. The introduction of the research background of spiro[4.4]nonane-1,6-diols;
2. The introduction of other chiral compounds with a C2 symmetry axis and their applications in asymmetric synthesis;
3. Based on the development of the semipinacol rearrangement in our group, we used chiral Brφnsted acid to promote a ring opening of the epoxy alcohol and reduced the products to obtain the chiral spiro[4.4]nonane-1,6-diols with three different stereochemistrys. This provides us a good foundation for further developing these compounds in asymmetric synthesis.
引文
[1]H. Leuchs; E. Gieseler, Ber.,45,2114(1912).
[2]H. Sutter; N. Wijkman,Ann.,519,97(1935).
[3](a) Cram, D. J.; Steinberg, H. J. Am. Chem. Soc.1954,76,2753. (b) Hawthorne, F.; Cram, D. J. J. Am. Chem. Soc.1952,74,5859. (c) Cram, D. J.; Daeniker, H. U. J. Am. Chem. Soc.1954, 76,2743.
[4]Hardegger, E.; Maeder, E.; Semarne, H. M.; Cram, D. J. J. Am. Chem. Soc.1959,81,2729.
[5](a) Horeau, A. Commpt. Rend.,226,2039(1949). (b) Cram, D. J.; van Duuren, B. L.J. Am. Chem. Soc.1955,77,3756.
[6]Schlesinger, H. I.; Brown, H. C.; Hoekstra, H. R.; Rapp, L. R. J. Am. Chem. Soc.1953,75, 199.
[7]Brewster, J. H. ibid.76,6362(1954).
[8]Dauben, W. G.; Fonken, G. J.; Noyce, D. S. ibid.78,2759(1956).
[9](a) Nakazaki, M.; Chikamatsu, H.; Asao, M. J. Org. Chem.1981,46,1147. (b)Nakazaki, M.; Chikamatsu, H.; Nishino, M.; Murakami, H. J. Org. Chem.1981,46,1151.
[10](a) Nakazaki, M.; Chikamatsu, H. Kagaku no Ryoiki 1977, 31,819. (b) Nakazaki, M.; Chikamatsu, H.; Naemura, K.; Hirose, Y.; Shimizu, T.; Asao, M. J. Chem. Soc., Chem. Commun.1978,668. (c) Nakazaki, M.; Chikamatsu, H.; Naemura, K.; Asao, M. J. Org. Chem.1980,45,4432.
[11](a) Nakazaki, M.; Chikamatsu, H.; Naemura, K.; Nishino, M.; Murakami, H.; Asao, M. J. Chem. Soc., Chem. Commun.1978,667. (b) Nakazaki, M.; Chikamatsu, H.; Naemura, K.; Nishino, M.; Murakami, H.; Asao, M. J. Org. Chem.1979,44,4588.
[12]Nieman, J. A.; Parvez, M.; Keay, B. A. Tetrahedron:Asymmetry 1993,4,1973-1976.
[13](a) Carruthers, W.; Orridge, A. J. Chem. Soc., Perkin Trans.1,1977,2411. (b) Gerlach, H.; Helv. Chim. Acta.1968,51,1587. (c) Gerlach, H.; Muller, W. Helv. Chim. Acta.1972,55, 2279. (d) Harada, N.; Ochiai, N.; Takada, K.; Uda, H. J. Chem. Soc., Chem. Commun. 1977,495. (e) Harada, N.; Ai, T.; Uda, H. J. Chem. Soc., Chem. Commun.1982,232.
[14]Chan, A. S. C.; Lin, C. C.; Sun, J.; Hu, W. H.; Li, Z.; Pan, W. D.; Mi, A. Q.; Jiang, Y. Z.; Huang, T. M.; Yang T. K.; Chen, J. H. Tetetrahedron:Asymmetry 1995,6(12),2953.
[15]Whitesell, J. K.Chem. Rev.1989,89,1581.
[16]Kagan, H. B.; Dang, T. P. J. Am. Chem. Soc. 1972,94,6249.
[17]Johnson, W. S.; Harbet, C. A.; Ratcliffe, G. E.; Stipanovic, R. O.J. Am. Chem. Soc.1976,98, 6188-93.
[18](a)Whitesell, J. K.; Felman, S. W. J. Org. Chem.1977,42,1663-4. (b) Whitesell, J. K. Acc. Chem. Res.1985,18,280-4.
[19](a) Harding, K. E.; Burks, S. R. J. Org. Chem.1981,46,3920-2. (b) Schlessinger, R. H.; Iwanowicz, E. J. Tetrahedron Lett.1987,28,2083-6.
[20](a) Hawkins, J. M.; Fu, G. C. J. Org. Chem.1986,51.2820-2. (b) Rudolf. K.; Hawkins, J. M.; Loncharich, R. J.; Houk, K. N. J. Org. Chem.1988,53,3879-82.
[21]Whitesell, J. K.; Felman, S. W.J. Org. Chem.1980.45,755-6.
[22](a) Kawanami, Y.; Ito, Y0; Kitagawa, T.; Taniguchi, Y.; Katsuki, T.; Yamaguchi, M. Tetrahedr- ron Lett.1984,25,857-60. (b) Ito, Y.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett.1984,25, 6015-6. (c) Ito, Y.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett.1985,26,4643-6. (d) Hanamoto, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett.1986,27,2463-4.
[23]Jadhav, P. K.; Bhat, K. S.; Perumal, P. T.; Brown, H. C. J. Org. Chem.1986,51,432-9.
[24](a) Masamune, S.; Kim, B. M.; Petersen, J. S.; Sato, T.; Veenstra, S. J.; Imai, T. J. Am. Chem. Soc.1985,107,4549-51. (b) Imai, T.; Tamura, T.; Yamamuro, A.; Sato, T.; Wollmann, T. A.; Kennedy, R. M.; Masamune, S. J. Am. Chem. Soc.1986,108,7402-4. (c) Masamune, S.; Kennedy, R. M.; Petersen, J. S. J. Am. Chem. Soc.1986,108,7404-5.
[25](a) Herold, T.; Schrott, U.; Hoffmann, R. W. Chem. Ber.1981,114,359-74. (b) Hoffmann, R. W.; Herold, T. Chem. Ber.1981,114,375-83. (c) Herold, T.; Hoffmann, R. W.Angew. Chem., Int. Ed. Engl.1978,17,768-9. (d) Hoffmann, R.; Hlbig, W. Chem. Ber.1982,115,2753.
[26](a) Roush, W.; Walts, A. E.; Hoong, L. K. J. Am. Chem. Soc.1985,107,8186-90. (b) Roush, W.; Halterman, R. L.J. Am. Chem. Soc.1986,108,295-6.
[27]Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc.1986,108,293-4.
[28]Haruta, R.; Ishiguro, R.; Ikeda, N.; Yamamoto, H.J. Am. Chem. Soc.1982,104,7667-9.
[29]Midland, M. M.; Preston, S. B. J. Am. Chem. Soc.1982,104,2330-1.
[30](a) Reetz, M. T.; Kunisch, F.; Heitmann, P. Tetrahedron Lett.1986,27,4721-4. (b) Sadhu, K. M.; Matteson, D. S.; Hurst, G. D.; Kurosky, J. M. Orgnometallics 1984,3,804-6.
[31]Grubbs, R. H.; Devries, R. A. Tetrahedron Lett.1977,1879-80.
[32]Tanaka, M.; Ikeda, Y.; Ogata, I. Chem. Lett.1975,1115-8.
[33]Hayashi, T.; Tanaka, M.; Ogata, I. Tetrahedron Lett.1977,295-6.
[34]Fryzuk, M. D.; Bosnich, B. J. Am. Chem. Soc.1977,99,6262-7.
[35]Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L.; Weinkauff, D. J. J. Am. Chem. Soc.1971,99,5946-52.
[36]Allen, D. L.; Gibson, V. C.; Green, M. L. H.; Skinner, J. F.; Grebenik, P. D. J. Chem. Soc., Chem. Commun.1983,895-6.
[37]Nagel, U. Angew. Chem., Int. Ed. Engl.1984,23,435-6.
[38]Miyashita, A.; Takaya, H.; Souchi, T.; Noyori, R. Tetrahedron 1984,40,1245-53.
[39]Bakos, J.; Tolh, I.; Heil, B.; Markow, L. J. Organomet. Chem.1985,279,23-9.
[40](a) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc.2005,127,1080-1081. (b) Gondi, V. B.; Gravel, M.; Rawal, V. H. Org. Lett.2005.7,5657. (c) Thadani, A. N.; Stankovic, A. R.; Rawal, V. H. PANS,2004,101,5846.
[41]Chan, A. S. C.; Hu, W. H.; Pei, C. C.; Lau, C. P.; Jiang, Y. Z.; Mi, A. Q.; Yan, M.; Sun, J.; Lou, R. L.; Deng, J. G.J. Am. Chem. Soc.1997,119,9570-9571.
[42]Pfenninger, A. Synthesis 1986,89-116.
[43](a) Mcnamara, J. M.; Kishi, Y. J. Am. Chem. Soc.1982,104,7371-2. (b) Sekizaki, H.; Jung, M.; Mcnamara, J. M.; Kishi, Y.J. Am. Chem. Soc.1982,104,7372-4. (c) Johnson, W. S.; Edington, C.; Elliott, J. D.; Silverman, I. R. J. Am. Chem. Soc.1984,106,7588-91.
[44](a) Tamura, Y.; Ko, T.; Kondo, H.; Annoura, H.; Fuji, M.; Takeuchi, R.; Fujioka, H. Tetrahedron Lett.1986,27,3859-60. (b) Mash, E. A.; Nelson, K. A. J. Am. Chem. Soc.1985, 107,8256-8. (c) Nelson, K. A.; Mash, E. A. J. Org. Chem.1986.57,2721-4.
[45](a) Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984,106,5004-5. (b) Maruoka, K.; Nakai, S.; Sakurai, M.; Yamamoto. H, Synthesis 1986, 130-1. (c) Mangeney, P.; Alexakis, A.; Normant, J. F. Tetrahedron Lett.1986,27,3143-6.
[46](a) Noyori, R.; Tomino, I.; Tanimoto, Y. J. Am. Chem. Soc.1979,101,3129-31. (b) Noyori, R.; Tomino, I.; Yamada, M.; Nishizawa, M. J. Am. Chem. Soc.1984,106,6717-25. (c) Noyori, R.; Tomino, I.; Tanimoto, Y.; Nishizawa, M.J. Am. Chem. Soc.1984,106,6709-16.
[47](a) Kelley, T. R.; Whiting, A.; Chandrakumar, N. S. J. Am. Chem. Soc.1986,108,3510-12. (b) Narasaka, K.; Inoue, M.; Okada, N. Chem. Lett.1986,1109-12.
[48](a) Schollkopf, U.; Hartwig, W.; Groth, U. Angew. Chem., Int. Ed. Engl.1979,18,863-4. (b) Mazaleyrat, J. P.; Cram, D. J.J. Am. Chem. Soc.1981,103,4585-6. (c) Hanessian, S.; Delorme, D.; Beaudoin, S.; Leblanc, Y. J. Am. Chem. Soc.1984,106,5754-6.
[49](a) Yamada, T.; Narasaka, K. Chem. Lett.1986,131-4. (b) Tokles, M.; Snyder, J. K. Tetrahed-ron Lett.1986,27,3951-4. (c) Tomioka, K.; Nakajima, M.; Koga, K. J. Am. Chem. Soc.1987, 109,6213-5.
[50]Sakamoto, A.; Yamamoto, Y,; Oda, J. J. Am. Chem. Soc.1987,109,7188-8.
[51]Tu, Y. Q.; Sun, L. D.; Wang, P. Z. J. Org. Chem.1999,64,629-633.
[52]Wang, F.; Tu, Y. Q.; Fan, C. A.; Wang, S. H.; Zhang, F. M. Tetetrahedron:Asymmetry 2002, 13,395-398.
[53]Wipf, P.; Jung, J. K.J. Org. Chem.2000,6319-6337.
[54]Miller, A. R.; Curtin, D. Y. J. Am. Chem. Soc.1976,98,1860.
[55]Zhu, S. S.; Cefalo, D. R.; La, D. S.; Jamieson, J. Y.; Davis, W. M.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc.1999,121,8251.
[56]Nakashima, D.; Yamamoto, H. J. Am. Chem. Soc.2006,128,9626.
[57]Storer, R. L.; Carrera, D. E.; Ni, Y.; MacMillan, D. W. C. J. Am. Chem. Soc.2006,128,84.
[2]H. Sutter; N. Wijkman,Ann.,519,97(1935).
[3](a) Cram, D. J.; Steinberg, H. J. Am. Chem. Soc.1954,76,2753. (b) Hawthorne, F.; Cram, D. J. J. Am. Chem. Soc.1952,74,5859. (c) Cram, D. J.; Daeniker, H. U. J. Am. Chem. Soc.1954, 76,2743.
[4]Hardegger, E.; Maeder, E.; Semarne, H. M.; Cram, D. J. J. Am. Chem. Soc.1959,81,2729.
[5](a) Horeau, A. Commpt. Rend.,226,2039(1949). (b) Cram, D. J.; van Duuren, B. L.J. Am. Chem. Soc.1955,77,3756.
[6]Schlesinger, H. I.; Brown, H. C.; Hoekstra, H. R.; Rapp, L. R. J. Am. Chem. Soc.1953,75, 199.
[7]Brewster, J. H. ibid.76,6362(1954).
[8]Dauben, W. G.; Fonken, G. J.; Noyce, D. S. ibid.78,2759(1956).
[9](a) Nakazaki, M.; Chikamatsu, H.; Asao, M. J. Org. Chem.1981,46,1147. (b)Nakazaki, M.; Chikamatsu, H.; Nishino, M.; Murakami, H. J. Org. Chem.1981,46,1151.
[10](a) Nakazaki, M.; Chikamatsu, H. Kagaku no Ryoiki 1977, 31,819. (b) Nakazaki, M.; Chikamatsu, H.; Naemura, K.; Hirose, Y.; Shimizu, T.; Asao, M. J. Chem. Soc., Chem. Commun.1978,668. (c) Nakazaki, M.; Chikamatsu, H.; Naemura, K.; Asao, M. J. Org. Chem.1980,45,4432.
[11](a) Nakazaki, M.; Chikamatsu, H.; Naemura, K.; Nishino, M.; Murakami, H.; Asao, M. J. Chem. Soc., Chem. Commun.1978,667. (b) Nakazaki, M.; Chikamatsu, H.; Naemura, K.; Nishino, M.; Murakami, H.; Asao, M. J. Org. Chem.1979,44,4588.
[12]Nieman, J. A.; Parvez, M.; Keay, B. A. Tetrahedron:Asymmetry 1993,4,1973-1976.
[13](a) Carruthers, W.; Orridge, A. J. Chem. Soc., Perkin Trans.1,1977,2411. (b) Gerlach, H.; Helv. Chim. Acta.1968,51,1587. (c) Gerlach, H.; Muller, W. Helv. Chim. Acta.1972,55, 2279. (d) Harada, N.; Ochiai, N.; Takada, K.; Uda, H. J. Chem. Soc., Chem. Commun. 1977,495. (e) Harada, N.; Ai, T.; Uda, H. J. Chem. Soc., Chem. Commun.1982,232.
[14]Chan, A. S. C.; Lin, C. C.; Sun, J.; Hu, W. H.; Li, Z.; Pan, W. D.; Mi, A. Q.; Jiang, Y. Z.; Huang, T. M.; Yang T. K.; Chen, J. H. Tetetrahedron:Asymmetry 1995,6(12),2953.
[15]Whitesell, J. K.Chem. Rev.1989,89,1581.
[16]Kagan, H. B.; Dang, T. P. J. Am. Chem. Soc. 1972,94,6249.
[17]Johnson, W. S.; Harbet, C. A.; Ratcliffe, G. E.; Stipanovic, R. O.J. Am. Chem. Soc.1976,98, 6188-93.
[18](a)Whitesell, J. K.; Felman, S. W. J. Org. Chem.1977,42,1663-4. (b) Whitesell, J. K. Acc. Chem. Res.1985,18,280-4.
[19](a) Harding, K. E.; Burks, S. R. J. Org. Chem.1981,46,3920-2. (b) Schlessinger, R. H.; Iwanowicz, E. J. Tetrahedron Lett.1987,28,2083-6.
[20](a) Hawkins, J. M.; Fu, G. C. J. Org. Chem.1986,51.2820-2. (b) Rudolf. K.; Hawkins, J. M.; Loncharich, R. J.; Houk, K. N. J. Org. Chem.1988,53,3879-82.
[21]Whitesell, J. K.; Felman, S. W.J. Org. Chem.1980.45,755-6.
[22](a) Kawanami, Y.; Ito, Y0; Kitagawa, T.; Taniguchi, Y.; Katsuki, T.; Yamaguchi, M. Tetrahedr- ron Lett.1984,25,857-60. (b) Ito, Y.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett.1984,25, 6015-6. (c) Ito, Y.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett.1985,26,4643-6. (d) Hanamoto, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett.1986,27,2463-4.
[23]Jadhav, P. K.; Bhat, K. S.; Perumal, P. T.; Brown, H. C. J. Org. Chem.1986,51,432-9.
[24](a) Masamune, S.; Kim, B. M.; Petersen, J. S.; Sato, T.; Veenstra, S. J.; Imai, T. J. Am. Chem. Soc.1985,107,4549-51. (b) Imai, T.; Tamura, T.; Yamamuro, A.; Sato, T.; Wollmann, T. A.; Kennedy, R. M.; Masamune, S. J. Am. Chem. Soc.1986,108,7402-4. (c) Masamune, S.; Kennedy, R. M.; Petersen, J. S. J. Am. Chem. Soc.1986,108,7404-5.
[25](a) Herold, T.; Schrott, U.; Hoffmann, R. W. Chem. Ber.1981,114,359-74. (b) Hoffmann, R. W.; Herold, T. Chem. Ber.1981,114,375-83. (c) Herold, T.; Hoffmann, R. W.Angew. Chem., Int. Ed. Engl.1978,17,768-9. (d) Hoffmann, R.; Hlbig, W. Chem. Ber.1982,115,2753.
[26](a) Roush, W.; Walts, A. E.; Hoong, L. K. J. Am. Chem. Soc.1985,107,8186-90. (b) Roush, W.; Halterman, R. L.J. Am. Chem. Soc.1986,108,295-6.
[27]Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc.1986,108,293-4.
[28]Haruta, R.; Ishiguro, R.; Ikeda, N.; Yamamoto, H.J. Am. Chem. Soc.1982,104,7667-9.
[29]Midland, M. M.; Preston, S. B. J. Am. Chem. Soc.1982,104,2330-1.
[30](a) Reetz, M. T.; Kunisch, F.; Heitmann, P. Tetrahedron Lett.1986,27,4721-4. (b) Sadhu, K. M.; Matteson, D. S.; Hurst, G. D.; Kurosky, J. M. Orgnometallics 1984,3,804-6.
[31]Grubbs, R. H.; Devries, R. A. Tetrahedron Lett.1977,1879-80.
[32]Tanaka, M.; Ikeda, Y.; Ogata, I. Chem. Lett.1975,1115-8.
[33]Hayashi, T.; Tanaka, M.; Ogata, I. Tetrahedron Lett.1977,295-6.
[34]Fryzuk, M. D.; Bosnich, B. J. Am. Chem. Soc.1977,99,6262-7.
[35]Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L.; Weinkauff, D. J. J. Am. Chem. Soc.1971,99,5946-52.
[36]Allen, D. L.; Gibson, V. C.; Green, M. L. H.; Skinner, J. F.; Grebenik, P. D. J. Chem. Soc., Chem. Commun.1983,895-6.
[37]Nagel, U. Angew. Chem., Int. Ed. Engl.1984,23,435-6.
[38]Miyashita, A.; Takaya, H.; Souchi, T.; Noyori, R. Tetrahedron 1984,40,1245-53.
[39]Bakos, J.; Tolh, I.; Heil, B.; Markow, L. J. Organomet. Chem.1985,279,23-9.
[40](a) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc.2005,127,1080-1081. (b) Gondi, V. B.; Gravel, M.; Rawal, V. H. Org. Lett.2005.7,5657. (c) Thadani, A. N.; Stankovic, A. R.; Rawal, V. H. PANS,2004,101,5846.
[41]Chan, A. S. C.; Hu, W. H.; Pei, C. C.; Lau, C. P.; Jiang, Y. Z.; Mi, A. Q.; Yan, M.; Sun, J.; Lou, R. L.; Deng, J. G.J. Am. Chem. Soc.1997,119,9570-9571.
[42]Pfenninger, A. Synthesis 1986,89-116.
[43](a) Mcnamara, J. M.; Kishi, Y. J. Am. Chem. Soc.1982,104,7371-2. (b) Sekizaki, H.; Jung, M.; Mcnamara, J. M.; Kishi, Y.J. Am. Chem. Soc.1982,104,7372-4. (c) Johnson, W. S.; Edington, C.; Elliott, J. D.; Silverman, I. R. J. Am. Chem. Soc.1984,106,7588-91.
[44](a) Tamura, Y.; Ko, T.; Kondo, H.; Annoura, H.; Fuji, M.; Takeuchi, R.; Fujioka, H. Tetrahedron Lett.1986,27,3859-60. (b) Mash, E. A.; Nelson, K. A. J. Am. Chem. Soc.1985, 107,8256-8. (c) Nelson, K. A.; Mash, E. A. J. Org. Chem.1986.57,2721-4.
[45](a) Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984,106,5004-5. (b) Maruoka, K.; Nakai, S.; Sakurai, M.; Yamamoto. H, Synthesis 1986, 130-1. (c) Mangeney, P.; Alexakis, A.; Normant, J. F. Tetrahedron Lett.1986,27,3143-6.
[46](a) Noyori, R.; Tomino, I.; Tanimoto, Y. J. Am. Chem. Soc.1979,101,3129-31. (b) Noyori, R.; Tomino, I.; Yamada, M.; Nishizawa, M. J. Am. Chem. Soc.1984,106,6717-25. (c) Noyori, R.; Tomino, I.; Tanimoto, Y.; Nishizawa, M.J. Am. Chem. Soc.1984,106,6709-16.
[47](a) Kelley, T. R.; Whiting, A.; Chandrakumar, N. S. J. Am. Chem. Soc.1986,108,3510-12. (b) Narasaka, K.; Inoue, M.; Okada, N. Chem. Lett.1986,1109-12.
[48](a) Schollkopf, U.; Hartwig, W.; Groth, U. Angew. Chem., Int. Ed. Engl.1979,18,863-4. (b) Mazaleyrat, J. P.; Cram, D. J.J. Am. Chem. Soc.1981,103,4585-6. (c) Hanessian, S.; Delorme, D.; Beaudoin, S.; Leblanc, Y. J. Am. Chem. Soc.1984,106,5754-6.
[49](a) Yamada, T.; Narasaka, K. Chem. Lett.1986,131-4. (b) Tokles, M.; Snyder, J. K. Tetrahed-ron Lett.1986,27,3951-4. (c) Tomioka, K.; Nakajima, M.; Koga, K. J. Am. Chem. Soc.1987, 109,6213-5.
[50]Sakamoto, A.; Yamamoto, Y,; Oda, J. J. Am. Chem. Soc.1987,109,7188-8.
[51]Tu, Y. Q.; Sun, L. D.; Wang, P. Z. J. Org. Chem.1999,64,629-633.
[52]Wang, F.; Tu, Y. Q.; Fan, C. A.; Wang, S. H.; Zhang, F. M. Tetetrahedron:Asymmetry 2002, 13,395-398.
[53]Wipf, P.; Jung, J. K.J. Org. Chem.2000,6319-6337.
[54]Miller, A. R.; Curtin, D. Y. J. Am. Chem. Soc.1976,98,1860.
[55]Zhu, S. S.; Cefalo, D. R.; La, D. S.; Jamieson, J. Y.; Davis, W. M.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc.1999,121,8251.
[56]Nakashima, D.; Yamamoto, H. J. Am. Chem. Soc.2006,128,9626.
[57]Storer, R. L.; Carrera, D. E.; Ni, Y.; MacMillan, D. W. C. J. Am. Chem. Soc.2006,128,84.