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

页码：5963 / 5966

页数：4

共 25 条

[1] Application of enantiopure templated azomethine ylids to β-hydroxy-α-amino acid synthesis
Alker, D
Hamblett, G
Harwood, LM
Robertson, SM
Watkin, DJ
Williams, CE
[J]. 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
BOLD, G
DUTHALER, RO
RIEDIKER, M
[J]. 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.
Cardillo, G
Gentilucci, L
Tolomelli, A
Tomasini, C
[J]. 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
DREWES, SE
MALISSAR, DGS
ROOS, GHP
[J]. CHEMISCHE BERICHTE, 1993, 126 (12) : 2663 - 2673
[6] ASYMMETRIC GLYCINE ENOLATE ALDOL REACTIONS - SYNTHESIS OF CYCLOSPORINES UNUSUAL AMINO-ACID, MEBMT
EVANS, DA
WEBER, AE
[J]. 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
GUANTI, G
BANFI, L
NARISANO, E
SCOLASTICO, C
[J]. TETRAHEDRON LETTERS, 1985, 26 (29) : 3517 - 3520

← 1 2 3 →