Asymmetric organic catalysis with modified cinchona alkaloids

被引：564

作者：

Tian, SK ^{[1
]}

Chen, YG ^{[1
]}

Hang, JF ^{[1
]}

Tang, L ^{[1
]}

McDaid, P ^{[1
]}

Deng, L ^{[1
]}

机构：

[1] Brandeis Univ, Dept Chem, Waltham, MA 02454 USA

来源：

ACCOUNTS OF CHEMICAL RESEARCH | 2004年 / 37卷 / 08期

关键词：

D O I：

10.1021/ar030048s

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Insights into the role played by modified cinchona alkaloids in the Sharpless asymmetric dihydroxylation inspired studies of modified cinchona alkaloids as chiral organic catalysts that lead to the development of highly enantio selective alcoholyses for the desymmetrization, kinetic resolution, and dynamic kinetic resolution of cyclic anhydrides, cyanation of ketones, and 1,4-addition of thiols to cylic enones. These studies demonstrate the potential of modified cinchona alkaloids as broadly useful chiral organic catalysts for asymmetric synthesis.

引用

页码：621 / 631

页数：11

共 53 条

[1] CATALYTIC ASYMMETRIC-SYNTHESIS OF HIGHLY FUNCTIONALIZED COMPOUNDS WITH 6 CONTIGUOUS STEREOCENTERS
AITKEN, RA
GOPAL, J
HIRST, JA
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (10) : 632 - 634
[2] Practical and highly enantioselective ring opening of cyclic meso-anhydrides mediated by cinchona alkaloids
Bolm, C
Schiffers, I
Dinter, CL
Gerlach, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (21) : 6984 - 6991
[3] Bolm C, 1999, SYNLETT, P195
[4] Catalytic, asymmetric dimerization of methylketene
Calter, MA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) : 8006 - 8007
[5] Asymmetric alcoholysis of cyclic anhydrides
Chen, YG
McDaid, P
Deng, L
[J]. CHEMICAL REVIEWS, 2003, 103 (08) : 2965 - 2983
[6] Parallel kinetic resolutions of monosubstituted succinic anhydrides catalyzed by a modified cinchona alkaloid
Chen, YG
Deng, L
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (45) : 11302 - 11303
[7] A highly enantioselective catalytic desymmetrization of cyclic anhydrides with modified cinchona alkaloids
Chen, YG
Tian, SK
Deng, L
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (39) : 9542 - 9543
[8] Choi CH, 2001, SYNTHESIS-STUTTGART, P1737
[9] RIGID AND HIGHLY ENANTIOSELECTIVE CATALYST FOR THE DIHYDROXYLATION OF OLEFINS USING OSMIUM TETRAOXIDE CLARIFIES THE ORIGIN OF ENANTIOSPECIFICITY
COREY, EJ
NOE, MC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (26) : 12579 - 12580
[10] Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO

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