Enantioselective reduction of imines catalyzed by a rhenium(V)-oxo complex

被引：157

作者：

Nolin, KA ^{[1
]}

Ahn, RW ^{[1
]}

Toste, FD ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 36期

关键词：

D O I：

10.1021/ja050831a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An air- and moisture-tolerant enantioselective hydrosilylation of N-phosphinyl imines employing a chiral Re(V)-oxo complex as a catalyst is described. The chiral catalyst is a cyanobis(oxazoline) (CNbox)-ligated rhenium-oxo complex of the general formula (CNbox)Re(O)Cl2(OPPh3). Using this catalyst, a wide range of aromatic imines (including cyclic, acyclic, and heteroaromatic), α-iminoesters, and α,β-unsaturated imines are reduced with good to excellent enantioselectivities. Copyright © 2005 American Chemical Society.

引用

页码：12462 / 12463

页数：2

共 41 条

[1]

BECKER R, 1985, ANGEW CHEM, V97, P969

[2] Vanadium-catalyzed asymmetric cyanohydrin synthesis [J].

Belokon, YN ;

North, M ;

Parsons, T .

ORGANIC LETTERS, 2000, 2 (11) :1617-1619

[3] ENANTIOSELECTIVE HYDROGENATION OF THE C=N GROUP - A CATALYTIC ASYMMETRIC REDUCTIVE AMINATION PROCEDURE [J].

BURK, MJ ;

FEASTER, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :6266-6267

[4] CATALYTIC ASYMMETRIC REDUCTIVE AMINATION OF KETONES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION OF THE C=N DOUBLE-BOND [J].

BURK, MJ ;

MARTINEZ, JP ;

FEASTER, JE ;

COSFORD, N .

TETRAHEDRON, 1994, 50 (15) :4399-4428

[5] ENANTIOSELECTIVE CONVERSION OF ALDEHYDES TO CYANOHYDRINS BY A CATALYTIC-SYSTEM WITH SEPARATE CHIRAL BINDING-SITES FOR ALDEHYDE AND CYANIDE COMPONENTS [J].

COREY, EJ ;

WANG, Z .

TETRAHEDRON LETTERS, 1993, 34 (25) :4001-4004

[6] A NEW ASYMMETRIC-SYNTHESIS OF CYANOHYDRINS AND OXYGEN-FUNCTIONALIZED DERIVATIVES - STEREOSELECTIVE ADDITION OF CYANIDE TO CHIRAL RHENIUM ALDEHYDE AND KETONE COMPLEXES OF THE FORMULA [(ETA-5-C5H5)RE(NO)(PPH3)(O=CRR')]+BF4- [J].

DALTON, DM ;

GARNER, CM ;

FERNANDEZ, JM ;

GLADYSZ, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6823-6829

[7] Rhenium-promoted diastereo- and enantioselective cyclopentannulation reactions: Furans as 1,3-propene dipoles [J].

Friedman, LA ;

You, F ;

Sabat, M ;

Harman, WD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (49) :14980-14981

[8] OXO-COMPLEXES OF RHENIUM(V) [J].

GROVE, DE ;

WILKINSON, G .

JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1966, (09) :1224-+

[9] Oxidations catalysed by rhenium(V) oxides 2. Clean sulfide oxidation by urea hydrogen peroxide [J].

Gunaratne, HQN ;

McKervey, MA ;

Feutren, S ;

Finlay, J ;

Boyd, J .

TETRAHEDRON LETTERS, 1998, 39 (31) :5655-5658

[10] A method for the asymmetric hydrosilylation of N-aryl imines [J].

Hansen, MC ;

Buchwald, SL .

ORGANIC LETTERS, 2000, 2 (05) :713-715

← 1 2 3 4 5 →