Catalytic atropo-enantioselective reduction of biaryl lactones to axially chiral biaryl compounds

被引：63

作者：

Ashizawa, Tomoko ^{[1
]}

Tanaka, Saiko ^{[1
]}

Yamada, Tohru ^{[1
]}

机构：

[1] Keio Univ, Dept Chem, Yokohama, Kanagawa 2238522, Japan

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 12期

关键词：

D O I：

10.1021/ol800802c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The atropo-enantioselective borohydride reduction with dynamic kinetic resolution of biaryl lactones was catalyzed by an optically active beta-ketoiminatocobalt(II) complex to afford optically active biaryl compounds. Chiral HPLC analysis of the starting biaryl lactones was performed at various temperatures to determine suitable reaction conditions for dynamic kinetic resolution. Various types of axially chiral biaryl compounds were obtained with high enantioselectivity.

引用

页码：2521 / 2524

页数：4

共 28 条

[1] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid
Akiyama, T
Itoh, J
Yokota, K
Fuchibe, K
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) : 1566 - 1568
[2] Catalytic asymmetric oxidative couplings of 2-naphthols by tridentate N-ketopinidene-based vanadyl dicarboxylates
Barhate, NB
Chen, CT
[J]. ORGANIC LETTERS, 2002, 4 (15) : 2529 - 2532
[3] The asymmetric Suzuki coupling route to axially chiral biaryls
Baudoin, O
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (20) : 4223 - 4229
[4] Novel concepts in directed biaryl synthesis, part 102. The directed synthesis of axially chiral ligands, reagents, catalysts, and natural products through the 'lactone methodology'
Bringmann, G
Tasler, S
Pfeifer, RM
Breuning, M
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 661 (1-2) : 49 - 65
[5] Novel concepts in directed biaryl synthesis, part 101. The lactone concept-a novel approach to the metal-assisted atroposelective construction of axially chiral biaryl systems
Bringmann, G
Breuning, M
Pfeifer, RM
Schenk, WA
Kamikawa, K
Uemura, M
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 661 (1-2) : 31 - 47
[6] Bringmann G, 2001, PROG CH ORG NAT PROD, V82, P1
[7] Novel concepts in directed biaryl synthesis - Part 77 - Atropo-enantioselective reduction of configurationally unstable biaryl lactones with BINAL-H
Bringmann, G
Breuning, M
[J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (02) : 385 - 390
[8] ATROPO-ENANTIOSELECTIVE BIARYL SYNTHESIS BY STEREOCONTROLLED CLEAVAGE OF CONFIGURATIVELY LABILE LACTONE-BRIDGED PRECURSORS USING CHIRAL H-NUCLEOPHILES
BRINGMANN, G
HARTUNG, T
[J]. TETRAHEDRON, 1993, 49 (36) : 7891 - 7902
[9] NOVEL CONCEPTS IN DIRECTED BIARYL SYNTHESIS .12. 1ST ATROPO-ENANTIOSELECTIVE RING-OPENING OF ACHIRAL BIARYLS CONTAINING LACTONE BRIDGES WITH CHIRAL HYDRIDE-TRANSFER REAGENTS DERIVED FROM BORANE
BRINGMANN, G
HARTUNG, T
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (06): : 761 - 762
[10] Novel concepts in directed biaryl synthesis, part 78. The lactone concept: An efficient pathway to axially chiral natural products and useful reagents
Bringmann, G
Breuning, M
Tasler, S
[J]. SYNTHESIS-STUTTGART, 1999, (04): : 525 - 558

← 1 2 3 →