Convenient synthesis of enantiopure cyclic alpha-hydroxyalkyl alpha-amino esters

被引：9

作者：

Andrews, MD

Brewster, AG

Moloney, MG

Owen, KL

机构：

[1] UNIV OXFORD,DYSON PERRINS LAB,OXFORD OX1 3QY,ENGLAND

[2] ZENECA PHARMACEUT,MACCLESFIELD SK10 4TG,CHESHIRE,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 03期

关键词：

D O I：

10.1039/p19960000227

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of cyclic alpha-hydroxyalkyl alpha-amino esters, the ring size of which varies varies from 4 to 7 members, in enantiopure form is readily achieved by intramolecular alkylative cyclisation of oxazolidine precursors.

引用

页码：227 / 228

页数：2

共 17 条

[1] ENANTIOSPECIFIC CONVERSION OF (S)-ALANINE TO (R)-ALPHA-METHYL PHENYLALANINE [J].

ALONSO, F ;

DAVIES, SG .

TETRAHEDRON-ASYMMETRY, 1995, 6 (02) :353-356

[2] TOTAL SYNTHESIS OF LACTACYSTIN [J].

COREY, EJ ;

REICHARD, GA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) :10677-10678

[3] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[4] INTRAMOLECULAR ALKYLATION OF CARBOXYLIC-ACIDS - APPLICATION TO THE SYNTHESIS OF BOC-PROTECTED CYCLIC AMINO-ACIDS [J].

DENICOLA, A ;

EINHORN, C ;

EINHORN, J ;

LUCHE, JL .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (07) :879-880

[5] RECENT DEVELOPMENTS IN THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS [J].

DUTHALER, RO .

TETRAHEDRON, 1994, 50 (06) :1539-1650

[6] AN EFFICIENT AND PRACTICAL TOTAL SYNTHESIS OF (+)-VINCAMINE FROM L-ASPARTIC ACID [J].

GMEINER, P ;

FELDMAN, PL ;

CHUMOYER, MY ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3068-3074

[7]

GROTH U, 1992, LIEBIGS ANN CHEM, P351

[8] ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS VIA CHIRAL N-ALKYLIDENESULFINAMIDES [J].

HUA, DH ;

LAGNEAU, N ;

WANG, H ;

CHEN, JS .

TETRAHEDRON-ASYMMETRY, 1995, 6 (02) :349-352

[9]

JEANGUENAT A, 1992, J CHEM SOC P1, P2291

[10] A REINVESTIGATION OF THE ALPHA-ALKYLATION OF 4-MONOSUBSTITUTED 2-PHENYLOXAZOL-5(4H)-ONES (AZLACTONES) - A GENERAL ENTRY INTO HIGHLY FUNCTIONALIZED ALPHA,ALPHA-DISUBSTITUTED ALPHA-AMINO-ACIDS [J].

OBRECHT, D ;

BOHDAL, U ;

RUFFIEUX, R ;

MULLER, K .

HELVETICA CHIMICA ACTA, 1994, 77 (05) :1423-1429

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