Highly Enantioselective Benzoin Condensation Reactions Involving a Bifunctional Protic Pentafluorophenyl-Substituted Triazolium Precatalyst

被引：130

作者：

Baragwanath, Louise ^{[1
]}

Rose, Christopher A. ^{[2
]}

Zeitler, Kirsten ^{[2
]}

Connon, Stephen J. ^{[1
]}

机构：

[1] Univ Dublin Trinity Coll, Sch Chem, Ctr Synth & Chem Biol, Dublin 2, Ireland

[2] Univ Regensburg, Inst Organ Chem, D-93053 Regensburg, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 23期

基金：

爱尔兰科学基金会;

关键词：

N-HETEROCYCLIC CARBENES; ASYMMETRIC INDUCTION; CHIRAL THIAZOLIUM; SALTS; CATALYSIS; KETENES;

D O I：

10.1021/jo902018j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Improved catalyst design by incorporating a hydrogen bond donating substituent to improve enantiocontrol together with an acidifying pentafluorophenyl substituent to enhance catalyst efficiency results in a triazolium ion precatalyst that promotes the asymmetric archetypal benzoin condensation with excellent efficiency and unprecedented enantioselectivity.

引用

页码：9214 / 9217

页数：4

共 37 条

[31] Asymmetric benzoin condensation catalyzed by chiral rotaxanes tethering a thiazolium salt moiety via the cooperation of the component: Can rotaxane be an effective reaction field?
Tachibana, Y
Kihara, N
Takata, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (11) : 3438 - 3439
[32] ASYMMETRIC BENZOIN CONDENSATION CATALYZED BY OPTICALLY-ACTIVE THIAZOLIUM SALTS IN MICELLAR 2-PHASE MEDIA
TAGAKI, W
TAMURA, Y
YANO, Y
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (02) : 478 - 480
[33] Modified chiral triazolium salts for enantioselective benzoin cyclization of enolizable keto-aldehydes: Synthesis of (+)-sappanone B
Takikawa, Hiroshi
Suzuki, Keisuke
[J]. ORGANIC LETTERS, 2007, 9 (14) : 2713 - 2716
[34] Wohler F., 1832, J ANN PHARM, V3, P249, DOI DOI 10.1002/JLAC.18320030302
[35] N-heterocyclic carbenes:: Organocatalysts displaying diverse modes of action
Zeitler, K.
[J]. ORGANOCATALYSIS, 2008, 2 : 183 - 206
[36] Extending mechanistic routes in heterazolium catalysis-promising concepts for versatile synthetic methods
Zeitler, K
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (46) : 7506 - 7510
[37] Chiral N-heterocyclic carbene catalyzed Staudinger reaction of ketenes with imines:: Highly enantioselective synthesis of N-boc β-lactams
Zhang, Yan-Rong
He, Lin
Wu, Xu
Shao, Pan-Lin
Ye, Song
[J]. ORGANIC LETTERS, 2008, 10 (02) : 277 - 280

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