以联萘酚(BINOL)为骨架的轴手性化合物在不对称催化中的研究进展
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摘要
具有C2对称轴的1,1'-联二萘酚(BINOL)具有非手性碳的手性旋光构型,此类分子的独特立体结构决定了分子兼具刚性和高的立体控制能力,以联萘酚为骨架衍生的一系列新颖的化合物以其优越的手性控制性能和手性催化剂方面的优良应用而备受关注。本文以有机合成中深具研究前景的不对称催化为切入点,综述了具有手性联萘酚结构的磷酸化合物、联萘酚金属磷酸盐化合物、联萘酚膦化合物以及相关衍生物在不对称催化反应中的研究进展。
1,1'-Binaphthol(BINOL) with C_2 symmetry was chiral optical configuration which has none chiral carbon.The unique spatial structure leads this type of molecule has high rigidity and stereo control ability.A series of novel chiral compounds derived from BINOL structure have provided their superior performance based on stereo control ability and the use of asymmetric catalysis.In this paper,we introduce the applications of the BINOL based complexes with optical activity,such as binaphthol chiral phosphoric acid,binaphthol metal phosphate,binaphthol phosphorus ligands and related derivatives in asymmetric catalytic reactions.
1,1'-Binaphthol(BINOL) with C_2 symmetry was chiral optical configuration which has none chiral carbon.The unique spatial structure leads this type of molecule has high rigidity and stereo control ability.A series of novel chiral compounds derived from BINOL structure have provided their superior performance based on stereo control ability and the use of asymmetric catalysis.In this paper,we introduce the applications of the BINOL based complexes with optical activity,such as binaphthol chiral phosphoric acid,binaphthol metal phosphate,binaphthol phosphorus ligands and related derivatives in asymmetric catalytic reactions.
引文
[1]RASMUSSEN O,AXELSSON O,TANNER D.A practical procedure for the solid phase synthesis of racemic 2,2'-dihydroxy-1,1'-binaphthyl[J].Synth Commun,1997,27(27):4027-4030.
[2]FERINGA B,WYNBERG H.Asymmetric phenol oxidation.Stereospecific and stereoselective oxidative coupling of a chiral tetrahydronaphthol[J].J Org Chem,1981,46(12):2547-2557.
[3]FERING B,WYNBERG H.Oxidative phenol couping with cupric-amine complexes[J].Tetrahedron Lett,1977,4447-4450.
[4]DOUSSOT J,GUY A,FERROUD C.Selective synthesis of 1,1'-binaphthalene derivatives by oxidative coupling with Ti Cl4[J].Tetrahedron Lett,2000,41,2545-2547.
[5]MATSUSHITA M,KAMATA K,YAMAGUCHI K,et al.Heterogeneously catalyzed aerobic oxidative biaryl coupling of 2-naphthols and substituted phenols in water[J].J Am Chem Soc,2005,127(18):6632-6640.
[6]AHMED I,CLARK A.Rapid synthesis of 3,3'-bisarylated binol derivatives using a C—H Borylation in Situ Suzuki-Miyaura coupling sequence[J].Org Lett,2014,16(16):4332-4335.
[7]BO Q,NIZAR H,SONIA R,et al.Ligand-accelerated stereoretentive Suzuki-Miyaura coupling of unprotected 3,3'-dibromo-binol[J].J Org Chem,2016,81(3):745-750.
[8]AKIYAMA T,ITOH J,YOKOTA K,et al.Enantioselective I Glaimich-type reaction catalyzed by a chiral Bronsted acid[J].Angew Chem Int Ed,2004,43(12):1566-1568.
[9]URAGUCHI D,TERADA M.Chiral Bronsted acidcatalyzed direct Mannich reactions via electrophilic activation[J].J Am Chem Soc,2004,126(17):5356-5357.
[10]GUO Q-X,LIU H,GUO C,et al.Chiral Bronsted acid-catalyzed direct asymmetric Maimich reaction[J].J Am Chem Soc,2007,129(13):3790-379.
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[12]URAGUCHI D,SORIMACHI K,TERADA M.Organocatalytic asymmetric aza-Friedel-Crafts alkylation of furan[J].J Am Chem Soc,2004,126(38):11804-11805.
[13]TERADA M,SORIMACHI K.Enantioselective Friedel-Crafts reaction of electron-rich alkenes catalyzed by chiral Bronsted acid[J].J Am Chem Soc,2007,129(2):292-293.
[14]KANG Q,ZHAO Z A,YOU S L.Highly enantioselective Friedel-Crafts reaction of indoles with imines by a chiral phosphoric acid[J].J Am Chem Soc,2007,129(6):1484-1485.
[15]ROWLAND B,ROWLAND B,ANTILLA C,et al.The highly enantioselective addition of indoles to Nacyl imines with use of a chiral phosphoric acid catalyst[J].Org Lett,2007,9(14):2609-2611.
[16]JIA Y X,ZHONG J,ZHU S F,et al.Chiral Bronsted acid catalyzed enantioselective FriedelCrafts reaction of indoles and a-aryl enamides:Construction of quaternary carbon atoms[J].Angew Chem Int Ed,2007,46(29):5565-5567.
[17]MURATORE M E,HOLLOWAY C A,PILLING A W,et al.Enantioselective Bronsted acid-catalyzed N-acyliminium cyclization cascades[J].J Am Chem Soc,2009,131(31):10796-10797.
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[19]AKIYAMA T,ITOH J,FUCHIBE K.Chiral Bronsted acid catalyzed enantioselective aza-Diels-Alder reaction of Brassard's diene with imines[J].Angew Chem Int Ed,2006,45(29):4796-4798.
[20]MOMIYAMA N,TABUSE H,TERADA M.Chiral phosphoric acid-govemed anti-diast-ereoselective and enantioselective hetero-Diels-Alder reaction of glyoxylate[J].J Am Chem Soc,2009,131(36):12882-12883.
[21]XING C,LIAO Y,NING J,et al.Optically active1,10-spirobiindane-7,70-diol(SPINOL)-based phosphoric acids as highly enantioselective catalysts for asymmetric organo catalysis[J].J Org Chem,2011,76(10):4125-31.
[22]孙哲,何金梅,屈孟男,等.共催化在有机合成反应中的研究进展[J].有机化学,2015,35(6):1250-1259.
[23]HENNECKE U,MULLER H,FROHLICH R.Enantioselective haloetherification by asymmetric opening of meso-halonim ions[J].Org Lett,2011,13:860-863.
[24]ALIX A,LALLI C,RETAILLEAU P,et al.Highly enantioselective electrophilicα-bromination of enecarbamates:Chiral phosphoric acid and calcium phosphate salt catalysts[J].J Am Chem Soc,2012,43(25):10389-10392.
[25]SAITO K,KAJIWARA Y,AKIYAMA T.Chiral copper(II)phosphate catalyzed enantioselective synthesis of isochromene derivatives by sequential intramolecular cyclization and asymmetric transfer hydrogenation of o-alkynylacetophenones[J].Angew Chem Int Ed,2013,52:13284-13288.
[26]TERADA M,LI F,TODA Y.Chiral silver phosphate catalyzed transformation of ortho-alkynylaryl ketones into 1h-isochromene derivatives through an intramolecular-cyclization/enantioselective-reduction sequence[J].Angew Chem Int Ed,2014,55:235-239.
[27]张军伟.手性布朗斯特酸催化的不对称加成反应研究[D].上海:华东理工大学,2014.
[28]INGLE G,MICHAEL G,JON M,et al.Lithium BINOL phosphate catalyzed desymmetrization of mesoepoxides with aromatic thiols[J].Org Lett,2014,16(21):5548-51.
[29]DENG Y,KARUNARATNE C,CSATARY E,et al.Chiral bimetallic catalysts derived from chiral metal phosphates:Enantioselective three-component asymmetric aza-Diels-Alder reactions of cyclic ketones[J].J Org Chem,2016,47(4):321-326.
[30]DOUGLAS C,OVERMAN L.Catalytic asymmetric synthesis of all-carbon quaternary stereocenters[J].Proc Natl Acad Sci,2004,101:5363-5367.
[31]TROST B,SILVERMAN S,STAMBULI J.Development of an asymmetric trimethylenemethane cycloaddition reaction:Application in the enantioselective synthesis of highly substitutedcarbocycles[J].J Am Chem Soc,2011,133:19483-19497.
[32]ISHIBASHI H,ISHIHARA K,YAMAMOTO H.A new artificial cyclase for polyprenoids:Enantioselective total synthesis of(-)-chromazonarol,(1)-8-epipuupehedione,and(-)-119-deoxytaondiol methyl ether[J].J Am Chem Soc,2004,126:11122-11123.
[33]SURENDRA K,RAJENDAR G,COREY J.Useful catalytic enantioselective cationic double annulation reactions initiated at an internal p-bond:Method and applications[J].J Am Chem Soc,2014,136:642-645.
[34]SCHAFROTH M A,SARLAH D,KRAUTWALD S,et al.Iridium-catalyzed enantioselective polyene cyclization[J].J Am Chem Soc,2012,134:20276-20278.
[35]FORTANET J,KESSLER F,BUCHWALD L.Palladium-catalyzed asymmetric dearomatization of naphthalene derivatives[J].J Am Chem Soc,2009,131:6676-6677.
[36]AIKAWA K,OKAMOTO T,MIKAMI K.Copper(I)-catalyzed asymmetric desymmetrization:Synthesis of five-membered-ring compounds containing all-carbon quaternary stereocenters[J].J Am Chem Soc,2012,134:10329-10332.
[2]FERINGA B,WYNBERG H.Asymmetric phenol oxidation.Stereospecific and stereoselective oxidative coupling of a chiral tetrahydronaphthol[J].J Org Chem,1981,46(12):2547-2557.
[3]FERING B,WYNBERG H.Oxidative phenol couping with cupric-amine complexes[J].Tetrahedron Lett,1977,4447-4450.
[4]DOUSSOT J,GUY A,FERROUD C.Selective synthesis of 1,1'-binaphthalene derivatives by oxidative coupling with Ti Cl4[J].Tetrahedron Lett,2000,41,2545-2547.
[5]MATSUSHITA M,KAMATA K,YAMAGUCHI K,et al.Heterogeneously catalyzed aerobic oxidative biaryl coupling of 2-naphthols and substituted phenols in water[J].J Am Chem Soc,2005,127(18):6632-6640.
[6]AHMED I,CLARK A.Rapid synthesis of 3,3'-bisarylated binol derivatives using a C—H Borylation in Situ Suzuki-Miyaura coupling sequence[J].Org Lett,2014,16(16):4332-4335.
[7]BO Q,NIZAR H,SONIA R,et al.Ligand-accelerated stereoretentive Suzuki-Miyaura coupling of unprotected 3,3'-dibromo-binol[J].J Org Chem,2016,81(3):745-750.
[8]AKIYAMA T,ITOH J,YOKOTA K,et al.Enantioselective I Glaimich-type reaction catalyzed by a chiral Bronsted acid[J].Angew Chem Int Ed,2004,43(12):1566-1568.
[9]URAGUCHI D,TERADA M.Chiral Bronsted acidcatalyzed direct Mannich reactions via electrophilic activation[J].J Am Chem Soc,2004,126(17):5356-5357.
[10]GUO Q-X,LIU H,GUO C,et al.Chiral Bronsted acid-catalyzed direct asymmetric Maimich reaction[J].J Am Chem Soc,2007,129(13):3790-379.
[11]Sickert M,Schrieider C.The enantioselective,Bronsted acid catalyzed,vinylogous Mannich reaction[J].Angew Chem Int Ed,2008,47:3631-3634.
[12]URAGUCHI D,SORIMACHI K,TERADA M.Organocatalytic asymmetric aza-Friedel-Crafts alkylation of furan[J].J Am Chem Soc,2004,126(38):11804-11805.
[13]TERADA M,SORIMACHI K.Enantioselective Friedel-Crafts reaction of electron-rich alkenes catalyzed by chiral Bronsted acid[J].J Am Chem Soc,2007,129(2):292-293.
[14]KANG Q,ZHAO Z A,YOU S L.Highly enantioselective Friedel-Crafts reaction of indoles with imines by a chiral phosphoric acid[J].J Am Chem Soc,2007,129(6):1484-1485.
[15]ROWLAND B,ROWLAND B,ANTILLA C,et al.The highly enantioselective addition of indoles to Nacyl imines with use of a chiral phosphoric acid catalyst[J].Org Lett,2007,9(14):2609-2611.
[16]JIA Y X,ZHONG J,ZHU S F,et al.Chiral Bronsted acid catalyzed enantioselective FriedelCrafts reaction of indoles and a-aryl enamides:Construction of quaternary carbon atoms[J].Angew Chem Int Ed,2007,46(29):5565-5567.
[17]MURATORE M E,HOLLOWAY C A,PILLING A W,et al.Enantioselective Bronsted acid-catalyzed N-acyliminium cyclization cascades[J].J Am Chem Soc,2009,131(31):10796-10797.
[18]AKIYAMA T,MORITA H,FUCHIBE K,et al.Chiral Bronsted acid-catalyzed inverse electron-demand aza diels-aider reaction[J].J Am Chem Soc,2006,128(40):13070-13071.
[19]AKIYAMA T,ITOH J,FUCHIBE K.Chiral Bronsted acid catalyzed enantioselective aza-Diels-Alder reaction of Brassard's diene with imines[J].Angew Chem Int Ed,2006,45(29):4796-4798.
[20]MOMIYAMA N,TABUSE H,TERADA M.Chiral phosphoric acid-govemed anti-diast-ereoselective and enantioselective hetero-Diels-Alder reaction of glyoxylate[J].J Am Chem Soc,2009,131(36):12882-12883.
[21]XING C,LIAO Y,NING J,et al.Optically active1,10-spirobiindane-7,70-diol(SPINOL)-based phosphoric acids as highly enantioselective catalysts for asymmetric organo catalysis[J].J Org Chem,2011,76(10):4125-31.
[22]孙哲,何金梅,屈孟男,等.共催化在有机合成反应中的研究进展[J].有机化学,2015,35(6):1250-1259.
[23]HENNECKE U,MULLER H,FROHLICH R.Enantioselective haloetherification by asymmetric opening of meso-halonim ions[J].Org Lett,2011,13:860-863.
[24]ALIX A,LALLI C,RETAILLEAU P,et al.Highly enantioselective electrophilicα-bromination of enecarbamates:Chiral phosphoric acid and calcium phosphate salt catalysts[J].J Am Chem Soc,2012,43(25):10389-10392.
[25]SAITO K,KAJIWARA Y,AKIYAMA T.Chiral copper(II)phosphate catalyzed enantioselective synthesis of isochromene derivatives by sequential intramolecular cyclization and asymmetric transfer hydrogenation of o-alkynylacetophenones[J].Angew Chem Int Ed,2013,52:13284-13288.
[26]TERADA M,LI F,TODA Y.Chiral silver phosphate catalyzed transformation of ortho-alkynylaryl ketones into 1h-isochromene derivatives through an intramolecular-cyclization/enantioselective-reduction sequence[J].Angew Chem Int Ed,2014,55:235-239.
[27]张军伟.手性布朗斯特酸催化的不对称加成反应研究[D].上海:华东理工大学,2014.
[28]INGLE G,MICHAEL G,JON M,et al.Lithium BINOL phosphate catalyzed desymmetrization of mesoepoxides with aromatic thiols[J].Org Lett,2014,16(21):5548-51.
[29]DENG Y,KARUNARATNE C,CSATARY E,et al.Chiral bimetallic catalysts derived from chiral metal phosphates:Enantioselective three-component asymmetric aza-Diels-Alder reactions of cyclic ketones[J].J Org Chem,2016,47(4):321-326.
[30]DOUGLAS C,OVERMAN L.Catalytic asymmetric synthesis of all-carbon quaternary stereocenters[J].Proc Natl Acad Sci,2004,101:5363-5367.
[31]TROST B,SILVERMAN S,STAMBULI J.Development of an asymmetric trimethylenemethane cycloaddition reaction:Application in the enantioselective synthesis of highly substitutedcarbocycles[J].J Am Chem Soc,2011,133:19483-19497.
[32]ISHIBASHI H,ISHIHARA K,YAMAMOTO H.A new artificial cyclase for polyprenoids:Enantioselective total synthesis of(-)-chromazonarol,(1)-8-epipuupehedione,and(-)-119-deoxytaondiol methyl ether[J].J Am Chem Soc,2004,126:11122-11123.
[33]SURENDRA K,RAJENDAR G,COREY J.Useful catalytic enantioselective cationic double annulation reactions initiated at an internal p-bond:Method and applications[J].J Am Chem Soc,2014,136:642-645.
[34]SCHAFROTH M A,SARLAH D,KRAUTWALD S,et al.Iridium-catalyzed enantioselective polyene cyclization[J].J Am Chem Soc,2012,134:20276-20278.
[35]FORTANET J,KESSLER F,BUCHWALD L.Palladium-catalyzed asymmetric dearomatization of naphthalene derivatives[J].J Am Chem Soc,2009,131:6676-6677.
[36]AIKAWA K,OKAMOTO T,MIKAMI K.Copper(I)-catalyzed asymmetric desymmetrization:Synthesis of five-membered-ring compounds containing all-carbon quaternary stereocenters[J].J Am Chem Soc,2012,134:10329-10332.