Aziridine 2-carboxylate ester mediated asymmetric synthesis of alpha-alkyl beta-amino acids

被引：47

作者：

Davis, FA

Reddy, GV

Liang, CH

机构：

[1] Department of Chemistry, Temple University, Philadelphia

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 29期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(97)01095-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The highly stereoselective ring opening of N-tosylaziridine 2-carboxylate esters with LiAlH4 followed by oxidation of the ensuing syn alcohols results in a highly efficient 4 step asymmetric synthesis of alpha-methyl beta-amino acids from N-sulfinylaziridine 2-carboxylate esters. (C) 1997 Elsevier Science Ltd.

引用

页码：5139 / 5142

页数：4

共 35 条

[1] ASYMMETRIC SYNTHESES OF 3-AMINO-2-METHYLPENTANOIC ACIDS - CONFIGURATIONS OF THE BETA-AMINO ACID IN MAJUSCULAMIDE C, 57-NORMAJUSCULAMIDE-C AND DOLASTATINS 11 AND 12
BATES, RB
GANGWAR, S
[J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (01) : 69 - 72
[2] Dolastatins .26. Synthesis and stereochemistry of dolastatin 11
Bates, RB
Brusoe, KG
Burns, JJ
Caldera, S
Cui, W
Gangwar, S
Gramme, MR
McClure, KJ
Rouen, GP
Schadow, H
Stessman, CC
Taylor, SR
Vu, VH
Yarick, GV
Zhang, JX
Pettit, GR
Bontems, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) : 2111 - 2113
[3] BEATTY MF, 1992, J CHEM SOC PERK T 1, P1637
[4] HIGHLY DIASTEREOSELECTIVE ALKYLATION OF PERHYDROPYRIMIDIN-4-ONES DIRECTED TOWARD THE SYNTHESIS OF ALPHA-SUBSTITUTED BETA-AMINO ACIDS .2.
BRASCHI, I
CARDILLO, G
TOMASINI, C
VENEZIA, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (24) : 7292 - 7298
[5] MANIPULATION OF SUBSTRATE-CONTROLLED DIASTEREOSELECTIVITIES IN HYDROBORATIONS IN ACYCLIC ALLYLAMINE DERIVATIVES
BURGESS, K
OHLMEYER, MJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) : 1027 - 1036
[6] ASYMMETRIC SYNTHESES OF OPTICALLY-ACTIVE ALPHA,BETA-DISUBSTITUTED BETA-AMINO ACIDS
BURGESS, K
LIU, LT
PAL, B
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) : 4758 - 4763
[7] Enzymatic resolution of alpha-alkyl beta-amino acids using immobilized penicillin G acylase
Cardillo, G
Tolomelli, A
Tomasini, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) : 8651 - 8654
[8] COLE DC, 1994, TETRAHEDRON, V50, P9517
[9] HIGHLY ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESIS OF BETA-AMINO ACID-ESTERS AND BETA-LACTAMS FROM ACHIRAL ESTERS AND IMINES
COREY, EJ
DECICCO, CP
NEWBOLD, RC
[J]. TETRAHEDRON LETTERS, 1991, 32 (39) : 5287 - 5290
[10] ASYMMETRIC-SYNTHESIS OF ANTI-ALPHA-ALKYL-BETA-AMINO ACIDS
DAVIES, SG
WALTERS, IAS
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (09): : 1129 - 1139

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