Highly enantioselective amination of α-substituted α-cyanoacetates with chiral catalysts accessible from both quinine and quinidine

被引：180

作者：

Liu, XF ^{[1
]}

Li, HM ^{[1
]}

Deng, L ^{[1
]}

机构：

[1] Brandeis Univ, Dept Chem, Waltham, MA 02454 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 02期

关键词：

D O I：

10.1021/ol048190w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic construction of nitrogen-substituted quaternary stereocenters is an important and challenging task in asymmetric synthesis. In this paper, we describe the use of 6'-OH-modified cinchona alkaloids that are accessible from either quinine or quinidine for the development of a highly enantioselective amination of alpha,alpha-disubstituted carbonyl compounds that is suitable for the creation of nitrogen-substituted quaternary stereocenters in either the R or S configuration.

引用

收藏

页码：167 / 169

页数：3

相关论文

共 36 条

[1]

Abellán T, 2000, EUR J ORG CHEM, V2000, P2689

[2] Enantiomerically enriched (R)- and (S)-α-methylphenylalanine via asymmetric PTC C-alkylation catalysed by NOBIN [J].

Belokon', YN ;

Kochetkov, KA ;

Churkina, TD ;

Ikonnikov, NS ;

Vyskocil, S ;

Kagan, HB .

TETRAHEDRON-ASYMMETRY, 1999, 10 (09) :1723-1728

[3] Asymmetric PTC C-alkylation mediated by TADDOL -: novel route to enantiomerically enriched α-alkyl-α-amino acids [J].

Belokon, YN ;

Kochetkov, KA ;

Churkina, TD ;

Ikonnikov, NS ;

Chesnokov, AA ;

Larionov, OV ;

Parmár, VS ;

Kumar, R ;

Kagan, HB .

TETRAHEDRON-ASYMMETRY, 1998, 9 (05) :851-857

[4] Chiral salen-metal complexes as novel catalysts for asymmetric phase transfer alkylations [J].

Belokon, YN ;

North, M ;

Kublitski, VS ;

Ikonnikov, NS ;

Krasik, PE ;

Maleev, VI .

TETRAHEDRON LETTERS, 1999, 40 (33) :6105-6108

[5] A practical asymmetric synthesis of α-methyl α-amino acids using a chiral Cu-salen complex as a phase transfer catalyst [J].

Belokon', YN ;

Davies, RG ;

North, M .

TETRAHEDRON LETTERS, 2000, 41 (37) :7245-7248

[6]

Bogevig A, 2002, ANGEW CHEM INT EDIT, V41, P1790, DOI 10.1002/1521-3773(20020517)41:10<1790::AID-ANIE1790>3.0.CO

[7]

2-Y

[8] Sc(BINOL)2Li:: a new heterobimetallic catalyst for the asymmetric Strecker reaction [J].

Chavarot, M ;

Byrne, JJ ;

Chavant, PY ;

Vallée, Y .

TETRAHEDRON-ASYMMETRY, 2001, 12 (08) :1147-1150

[9] Proline-catalyzed asymmetric α-amination of aldehydes and ketones -: An astonishingly simple access to optically active α-hydrazino carbonyl compounds [J].

Duthaler, RO .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (09) :975-978

[10] Chiral magnesium bis(sulfonamide) complexes as catalysts for the merged enolization and enantioselective amination of N-acyloxazolidinones. A catalytic approach to the synthesis of arylglycines [J].

Evans, DA ;

Nelson, SG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (27) :6452-6453

← 1 2 3 4 →