Design of chiral bifunctional secondary amine catalysts for asymmetric enamine catalysis

被引：65

作者：

Kano, Taichi ^{[1
]}

Maruoka, Keiji ^{[1
]}

机构：

[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan

来源：

CHEMICAL COMMUNICATIONS | 2008年 / 43期

关键词：

D O I：

10.1039/b809301f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of binaphthyl-based secondary amine catalysts containing various functional groups have been designed as new chiral bifunctional amine catalysts. These chiral organocatalysts have been successfully applied to several asymmetric reactions via enamine intermediates and exhibit unique reactivity and selectivity in comparison with proline and its derivatives.

引用

页码：5465 / 5473

页数：9

共 46 条

[1] The nitroso ene reaction: A regioselective and stereoselective allylic nitrogen functionalization of mechanistic delight and synthetic potential [J].

Adam, W ;

Krebs, O .

CHEMICAL REVIEWS, 2003, 103 (10) :4131-4146

[2] Enantioselective organocatalytic α-fluorination of aldehydes [J].

Beeson, TD ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (24) :8826-8828

[3]

Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677

[4] Organocatalytic asymmetric α-bromination of aldehydes and ketones [J].

Bertelsen, S ;

Halland, N ;

Bachmann, S ;

Marigo, M ;

Braunton, A ;

Jorgensen, KA .

CHEMICAL COMMUNICATIONS, 2005, (38) :4821-4823

[5] Direct and enantioselective organocatalytic α-chlorination of aldehydes [J].

Brochu, MP ;

Brown, SP ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4108-4109

[6] The direct and enantioselective organocatalytic α-oxidation of aldehydes [J].

Brown, SP ;

Brochu, MP ;

Sinz, CJ ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10808-10809

[7] A highly enantioselective route to either enantiomer of both α- and β-amino acid derivatives [J].

Córdova, A ;

Watanabe, S ;

Tanaka, F ;

Notz, W ;

Barbas, CF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1866-1867

[8]

Dalko P. I., 2007, ENANTIO SELECTIVE OR

[9]

Dalko PI, 2001, ANGEW CHEM INT EDIT, V40, P3726, DOI 10.1002/1521-3773(20011015)40:20<3726::AID-ANIE3726>3.0.CO

[10]

2-D

← 1 2 3 4 5 →