Highly diastereoselective synthesis of trans-3,4-(difluoromethano)glutamic acid

被引：40

作者：

Shibuya, A ^{[1
]}

Kurishita, M ^{[1
]}

Ago, C ^{[1
]}

Taguchi, T ^{[1
]}

机构：

[1] TOKYO COLL PHARM,HACHIOJI,TOKYO 19203,JAPAN

来源：

TETRAHEDRON | 1996年 / 52卷 / 01期

关键词：

D O I：

10.1016/0040-4020(95)00870-E

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of enantiomerically pure N-(4'-bromo-4',4'-difluorocrotonoyl)oxazolidinone 5 with lithium enolate of N-diphenylmethyldeneglycinate 6 in DMF proceeded in highly diastereoselective manner to give trans-disubstituted gem-difluorocyclopropane 7, which was readily converted to the 3,4-(difluoro- methano)glutamic acid 4.

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页码：271 / 278

页数：8

相关论文

共 29 条

[1] ASYMMETRIC SYNTHESES OF ALL 4 STEREOISOMERS OF 2,3-METHANOMETHIONINE [J].

BURGESS, K ;

HO, KK .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) :5931-5936

[2] ENANTIOSELECTIVE METHYLATION OF GLYCINE INFLUENCE OF THE STRUCTURE OF THE CHIRAL NUCLEOFUGAL [J].

DUHAMEL, P ;

EDDINE, JJ ;

VALNOT, JY .

TETRAHEDRON LETTERS, 1987, 28 (33) :3801-3804

[3] THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS - ELECTROPHILIC AZIDATION OF CHIRAL IMIDE ENOLATES, A PRACTICAL APPROACH TO THE SYNTHESIS OF (R)-ALPHA-AZIDO AND (S)-ALPHA-AZIDO CARBOXYLIC-ACIDS [J].

EVANS, DA ;

BRITTON, TC ;

ELLMAN, JA ;

DOROW, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :4011-4030

[4]

Hughes D.L., 1992, ORG REACT, V42, P335, DOI [10.1002/0471264180.OR042.02, DOI 10.1002/0471264180.OR042.02]

[5]

KIRK KL, 1991, ACS SYM SER, V456, P136

[6] SYNTHESIS OF CYCLOPROPANE AMINO-ACIDS AND THEIR INCORPORATION INTO BIOACTIVE PEPTIDES AS CONFORMATIONAL CONSTRAINT [J].

KODAMA, H ;

SHIMOHIGASHI, Y .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1994, 52 (03) :180-191

[7]

Lin H.-W., 1987, CHEM CYCLOPROPYL GRO

[8] MECHANISM OF CYTOCHROME-P-450 INHIBITION BY CYCLOPROPYLAMINES [J].

MACDONALD, TL ;

ZIRVI, K ;

BURKA, LT ;

PEYMAN, P ;

GUENGERICH, FP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (07) :2050-2052

[9] A CATALYTIC ENANTIOSELECTIVE SYNTHESIS OF ALPHA-METHYL AMINO-ACID DERIVATIVES BY PHASE-TRANSFER CATALYSIS [J].

ODONNELL, MJ ;

WU, SD .

TETRAHEDRON-ASYMMETRY, 1992, 3 (05) :591-594

[10] A MILD AND EFFICIENT ROUTE TO SCHIFF-BASE DERIVATIVES OF AMINO-ACIDS [J].

ODONNELL, MJ ;

POLT, RL .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (13) :2663-2666