两性水溶性手性膦配体的合成
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摘要
为了得到光学纯化合物人们采取了许多办法,其中采用手性催化剂进行不对称合成的方法更是成为其中的热点,但是催化剂的回收困难造成成本提高限制它们进一步的应用。为了解决这个问题,本论文首先合成了PPM,在此基础上对其进行修饰得到新型两性水溶性手性膦配体;然后又合成了两种BINAP的5,5’位衍生物,并尝试用类似的方法用氨基酸进行修饰。本文内容主要包括以下部分:
(1)以N-BOC-4-羟基-L-脯氨酸甲酯为原料,经四步合成了PPM。然后以PPM为母体合成了一种新型的手性膦配体—氨基酸型两性水溶性手性膦配体和两个中间体。手性膦配体及其中间体结构被1H NMR,31P NMR和13C NMR鉴定。以上合成的化合物均为新化合物,未见文献报道。
(2)以BINOL为原料,合成了BINAP,然后通过两条不同的反应路线将官能团引入到BINAP上,合成了两种BINAP 5,5’位衍生物,最后对这两种衍生物尝试做近一步的修饰,将氨基酸基团组装到分子结构中。
In order to get optically pure compounds, people do a lot of efforts, and the use of chiral catalysts for asymmetric synthesis is one of the most effective ways. But the difficulty of catalyst recovery limits their further application. To solve this problem, this thesis synthesis PPM at first, and then modified PPM to get a new zwitterionic water-soluble and chiral diphosphine ligand. Next, we synthesized BINAP and two BINAP derivatives, and try to modify them at the similar way. This thesis mainly includes :
(1)Using 4-Hydroxy-L-proline as the starting material, PPM was prepared in four steps. And then a new zwitterionic water-soluble chiral phosphine ligand with amino acid moieties was prepared. The structure of new phosphine and precursors were identified by 1H NMR、13C NMR and 31P NMR.
(2) BINAP was synthesized from BINOL, then using BINAP as the starting material, two BINAP derivatives: 5,5’-Diamino BINAP and 5,5’- Diaminomethyl BINAP were prepared. Finally, the two derivatives was tried to be modified with amino acids at the similar way.
(1)以N-BOC-4-羟基-L-脯氨酸甲酯为原料,经四步合成了PPM。然后以PPM为母体合成了一种新型的手性膦配体—氨基酸型两性水溶性手性膦配体和两个中间体。手性膦配体及其中间体结构被1H NMR,31P NMR和13C NMR鉴定。以上合成的化合物均为新化合物,未见文献报道。
(2)以BINOL为原料,合成了BINAP,然后通过两条不同的反应路线将官能团引入到BINAP上,合成了两种BINAP 5,5’位衍生物,最后对这两种衍生物尝试做近一步的修饰,将氨基酸基团组装到分子结构中。
In order to get optically pure compounds, people do a lot of efforts, and the use of chiral catalysts for asymmetric synthesis is one of the most effective ways. But the difficulty of catalyst recovery limits their further application. To solve this problem, this thesis synthesis PPM at first, and then modified PPM to get a new zwitterionic water-soluble and chiral diphosphine ligand. Next, we synthesized BINAP and two BINAP derivatives, and try to modify them at the similar way. This thesis mainly includes :
(1)Using 4-Hydroxy-L-proline as the starting material, PPM was prepared in four steps. And then a new zwitterionic water-soluble chiral phosphine ligand with amino acid moieties was prepared. The structure of new phosphine and precursors were identified by 1H NMR、13C NMR and 31P NMR.
(2) BINAP was synthesized from BINOL, then using BINAP as the starting material, two BINAP derivatives: 5,5’-Diamino BINAP and 5,5’- Diaminomethyl BINAP were prepared. Finally, the two derivatives was tried to be modified with amino acids at the similar way.
引文
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[86]王俊,光学活性2,2’-双二苯基膦基-1,1’联萘(BINAP)的合成及功能性5,5-二甲基海因衍生物的合成研究. [学位论文]上海:华东师范大学, 2004.
[2] Rouchi A M. Fine chemicals companies are jockeying for position to deliver the increasingly complicated chiral small molecules of the future [J], Chem. Eng. News, 2003,81(18): 45-55.
[3] Vcloo R A, Koomen G J. Synthesis of enantiomerically pure (S)-(?)-propranolol from sorbitol [J], Tetrahedron: Asymmetry, 1993, 4(12): 2401-2404.
[4] Blaschke G, Kraft H P, Markgraf H. Chem. Ber. Optical resolution of thalidomide and other glutarimide derivatives [J], Chem.Ber., 1980, 113: 2318-2322.
[5] Knowles, W. S.; Sabacky, M.Catalytic asymmetric hydrogenation employing a soluble, optically active, rhodium complex [J], J.Chem.Commun., 1968, 22: 1445-1446.
[6] Kagan, H. B.; Dang, T. P. Asymmetric catalytic reduction with transition metal complexes. I. Catalytic system of rhodium(I) with (-)-2,3-0-isopropylidene-2,3-dihydroxy-1,4-bis (diphenylphosphino)butane, a new chiral diphosphine [J], J. Am. Chem. Soc., 1972, 94(18): 6429-6433.
[7] Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. Synthesis of 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP), an atropisomeric chiral bis(triaryl)phosphine, and its use in the rhodium(I)-catalyzed asymmetric hydrogenation of .alpha.-(acylamino)acrylic acids [J], J. Am. Chem. Soc., 1980, 102(27): 7932-7934.
[8] Research by topic on SciFinder Scholar, 2004-08-27. Keyword BINAP and then refine by document type.
[9] http://www.rhodia-ppd.com.
[10] Akutagawa, S. Asymmetric synthesis by metal BINAP catalysts [J], Appl. Catal. A, 1995, 128(2): 171-207.
[11] Noyori, R. Asymmetric Catalysis in Organic Synthesis[M], New York: John Wiley & Sons, 1994; Chapter 1.
[12] Bergens, S. H.; Nohada, P.; Whelan, J.; Bosnich, B. Asymmetric catalysis. Production of chiral diols by enantioselective catalytic intramolecular hydrosilation of olefins [J], J. Am. Chem.Soc., 1992, 114(6): 2121-2128.
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