α-Hydroxy carboxylic acids as ligands for enantioselective diethylzinc additions to aromatic and aliphatic aldehydes

被引：45

作者：

Bauer, T ^{[1
]}

Gajewiak, J ^{[1
]}

机构：

[1] Warsaw Univ, Dept Chem, PL-020093 Warsaw, Poland

来源：

TETRAHEDRON | 2004年 / 60卷 / 41期

关键词：

diethylzinc; titanium tetraisopropoxide; alpha-hydroxy acids; aldehydes; enantioselective;

D O I：

10.1016/j.tet.2004.07.060

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first examples of the enantioselective titanium-mediated diethylzinc additions to aromatic and aliphatic aldehydes catalyzed by optically active alpha-hydroxy acids are presented. The reactions proceed with very good yield and good asymmetric induction. Enantioselectivities up to 90% are obtained depending on ligand and aldehyde used. A stereochemical model for the reaction is proposed. (C) 2004 Elsevier Ltd. All rights reserved.

引用

收藏

页码：9163 / 9170

页数：8

相关论文

共 36 条

[1] Enantioselective addition of dialkylzinc to aldehydes catalyzed by (S)-2-(N,N-disubstituted aminomethyl)indoline [J].

Asami, M ;

Watanabe, H ;

Honda, K ;

Inoue, S .

TETRAHEDRON-ASYMMETRY, 1998, 9 (23) :4165-4173

[2]

Aurich HG, 1997, LIEBIGS ANN-RECL, P423

[3] Diastereoselective synthesis of 2-alkoxy-5-tert-butylmandelic acid [J].

Bauer, T ;

Gajewiak, J .

SYNTHESIS-STUTTGART, 2004, (01) :20-22

[4] α-hydroxy carboxylic acids:: new ligands for diethylzinc additions to aldehydes [J].

Bauer, T ;

Tarasiuk, J .

TETRAHEDRON LETTERS, 2002, 43 (04) :687-689

[5] ALIPHATIC HYDROXY-ACIDS .3. SYNTHESES WITH ALKYL 2-ACETOXY-3-CARBOXYPROPIONATES [J].

BRETTLE, R ;

LATHAM, DW .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (08) :906-&

[6] CONFIGURATION OF CARBOHYDRATES, HYDROXY-ACIDS AND AMINO-ACIDS [J].

BREWSTER, P ;

HUGHES, ED ;

INGOLD, CK ;

RAO, PADS .

NATURE, 1950, 166 (4213) :178-179

[7] The formyl C-H•••O hydrogen bond as a critical factor in enantioselective Lewis-acid catalyzed reactions of aldehydes [J].

Corey, EJ ;

Lee, TW .

CHEMICAL COMMUNICATIONS, 2001, (15) :1321-1329

[8] Chiral ligands derived from abrine.: Part 6:: Importance of a bulky N-alkyl group in indole-containing chiral β-tertiary amino alcohols for controlling enantioselectivity in addition of diethylzinc toward aldehydes [J].

Dai, WM ;

Zhu, HJ ;

Hao, XJ .

TETRAHEDRON-ASYMMETRY, 2000, 11 (11) :2315-2337

[9] SYNTHESIS OF N-15-LABELED CHIRAL BOC-AMINO ACIDS FROM TRIFLATES - ENANTIOMERS OF LEUCINE AND PHENYLALANINE [J].

DEGERBECK, F ;

FRANSSON, B ;

GREHN, L ;

RAGNARSSON, U .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (01) :11-14

[10]

Draanen N. A., 1991, J ORG CHEM, V56, P2499

← 1 2 3 4 →