syn-selective boron mediated aldol condensations for the asymmetric synthesis of β-hydroxy-α-amino acids

被引：26

作者：

Caddick, S ^{[1
]}

Parr, NJ

Pritchard, MC

机构：

[1] Univ Sussex, Sch Chem Phys & Environm Sci, Ctr Biomol Design & Drug Dev, Brighton BN1 9QJ, E Sussex, England

[2] Parke Davis NRC, Cambridge CB2 2QB, England

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 31期

基金：

英国工程与自然科学研究理事会;

关键词：

aldol; beta-hydroxy-alpha-amino acids; glycine enolates; boron; imidazolidinone; asymmetric synthesis;

D O I：

10.1016/S0040-4039(00)00734-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Imidazolidinone-bound glycine enolate derivatives have been shown to undergo aldol condensation with aromatic and aliphatic aldehydes in good yields and with excellent stereocontrol (62-84%, 93-95% d.e.). Removal of the pendant imidazolidinone auxiliary and hydrogenolysis affords the beta-hydroxy-alpha-amino acid derivatives. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：5963 / 5966

页数：4

相关论文

共 25 条

[1] Application of enantiopure templated azomethine ylids to β-hydroxy-α-amino acid synthesis [J].

Alker, D ;

Hamblett, G ;

Harwood, LM ;

Robertson, SM ;

Watkin, DJ ;

Williams, CE .

TETRAHEDRON, 1998, 54 (22) :6089-6098

[2] ENANTIOSELECTIVE SYNTHESES WITH TITANIUM-CARBOHYDRATE COMPLEXES .3. ENANTIOSELECTIVE SYNTHESIS OF D-THREO-BETA-HYDROXY-ALPHA-AMINO ACIDS WITH TITANIUM-CARBOHYDRATE COMPLEXES [J].

BOLD, G ;

DUTHALER, RO ;

RIEDIKER, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (04) :497-498

[3] Ring expansion of N-acyl aziridine-2-imides to oxazoline-4-imides, useful precursors of pure beta-hydroxy alpha-aminoacids. [J].

Cardillo, G ;

Gentilucci, L ;

Tolomelli, A ;

Tomasini, C .

TETRAHEDRON LETTERS, 1997, 38 (39) :6953-6956

[4]

CIMARUSTI CM, 1983, CHEM BRIT, V19, P302

[5] EPHEDRINE-DERIVED IMIDAZOLIDIN-2-ONES - BROAD UTILITY CHIRAL AUXILIARIES IN ASYMMETRIC-SYNTHESIS [J].

DREWES, SE ;

MALISSAR, DGS ;

ROOS, GHP .

CHEMISCHE BERICHTE, 1993, 126 (12) :2663-2673

[6] ASYMMETRIC GLYCINE ENOLATE ALDOL REACTIONS - SYNTHESIS OF CYCLOSPORINES UNUSUAL AMINO-ACID, MEBMT [J].

EVANS, DA ;

WEBER, AE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (21) :6757-6761

[7]

Grandel R, 1996, LIEBIGS ANN, P1143

[8]

Grandel R, 1998, EUR J ORG CHEM, V1998, P409, DOI 10.1002/(SICI)1099-0690(199802)1998:2<409::AID-EJOC409>3.0.CO

[9]

2-2

[10] ACID CATALYSIS IN ALDOL CONDENSATION OF ALPHA-AMINO SILYL KETENE ACETALS - DIASTEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-BETA-HYDROXYACIDS [J].

GUANTI, G ;

BANFI, L ;

NARISANO, E ;

SCOLASTICO, C .

TETRAHEDRON LETTERS, 1985, 26 (29) :3517-3520