A new functionalized, chiral disulfide derived from L-cysteine:: (R,R)-bis[(3-benzyloxazolan-4-yl)-methane] disulfide as a catalyst in the diethylzinc addition to aldehydes

被引：55

作者：

Braga, AL ^{[1
]}

Appelt, HR

Schneider, PH

Silveira, CC

Wessjohann, LA

机构：

[1] Univ Fed Santa Maria, Dept Quim, BR-97105900 Santa Maria, RS, Brazil

[2] Univ Munich, Inst Organ Chem, D-80333 Munich, Germany

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 09期

关键词：

D O I：

10.1016/S0957-4166(99)00145-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A new, easily accessible, chiral disulfide 3 was prepared from L-cysteine in a short synthetic sequence (Scheme 1) and applied successfully as a highly efficient catalyst for the enantioselective addition of diethyl zinc to aromatic and aliphatic aldehydes to afford the product alcohols in up to more than 99% ee. In contrast to the more common amino alcohols used in similar reactions, catalyst 3 does not have a protic hydrogen in the form of a free hydroxy group. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1733 / 1738

页数：6

共 23 条

[11] ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALPHA-BRANCHED ALDEHYDES [J].

KANG, J ;

LEE, JW ;

KIM, JI .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (17) :2009-2010

[12] (Nonracemic) thiols and Zn-II. Structural and catalytic aspects of some natural and non-natural zinc thiolates [J].

Kellogg, RM ;

Hof, RP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (14) :1651-1657

[13] Organozinc mediated reactions [J].

Knochel, P ;

Perea, JJA ;

Jones, P .

TETRAHEDRON, 1998, 54 (29) :8275-8319

[14] Synthesis of C2-symmetrical bis-β-amino alcohols from (R)-cysteine and their application in enantioselective catalysis [J].

Kossenjans, M ;

Martens, J .

TETRAHEDRON-ASYMMETRY, 1998, 9 (08) :1409-1417

[15] ENANTIOSELECTIVE ADDITION OF ORGANOMETALLIC REAGENTS TO CARBONYL-COMPOUNDS - CHIRALITY TRANSFER, MULTIPLICATION, AND AMPLIFICATION [J].

NOYORI, R ;

KITAMURA, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (01) :49-69

[16]

Noyori R., 1994, ASYMMETRIC CATALYSIS

[17] APPLICATION OF N,S-CHELATING CHIRAL ZINC BIS(ARENETHIOLATE) COMPLEXES AS NEW PRECURSOR CATALYSTS IN THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES [J].

RIJNBERG, E ;

JASTRZEBSKI, JTBH ;

JANSSEN, MD ;

BOERSMA, J ;

VANKOTEN, G .

TETRAHEDRON LETTERS, 1994, 35 (35) :6521-6524

[18] PREPARATION OF FUNCTIONALIZED DIALKYLZINC REAGENTS VIA AN IODINE ZINC EXCHANGE-REACTION - HIGHLY ENANTIOSELECTIVE SYNTHESIS OF FUNCTIONALIZED SECONDARY ALCOHOLS [J].

ROZEMA, MJ ;

SIDDURI, A ;

KNOCHEL, P .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :1956-1958

[19]

SINGH VK, 1992, SYNTHESIS-STUTTGART, P843

[20] ENANTIOSELECTIVE ADDITION OF ORGANOZINC REAGENTS TO ALDEHYDES [J].

SOAI, K ;

NIWA, S .

CHEMICAL REVIEWS, 1992, 92 (05) :833-856

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