SYNTHESIS OF PROTECTED 3-METHYLASPARTIC ACIDS FROM GLUTAMIC ANHYDRIDE VIA NICKELACYCLES

被引：16

作者：

CASTANO, AM

ECHAVARREN, AM

机构：

[1] CSIC,INST QUIM ORGAN,JUAN CIERVA 3,E-28006 MADRID,SPAIN

[2] UNIV AUTONOMA MADRID,DEPT QUIM,E-28049 MADRID,SPAIN

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 27期

关键词：

D O I：

10.1016/S0040-4039(00)79352-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of fully protected beta-methyl aspartic acids from (+/-)-glutamic anhydride has been achieved by means of ring contraction of the derived nickelacycle followed by insertion of an isocyanide. The intermediate five-membered ring nickelacycles were isolated and characterized spectroscopically.

引用

页码：4361 / 4362

页数：2

共 17 条

[1] ENANTIOSPECIFIC SYNTHESIS OF DEALANYLALAHOPCIN
BALDWIN, JE
ADLINGTON, RM
GOLLINS, DW
SCHOFIELD, CJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (09) : 720 - 721
[2] ASYMMETRIC AMINO-ACID SYNTHESIS - PREPARATION OF THE BETA-ANION DERIVED FROM ASPARTIC-ACID
BALDWIN, JE
MOLONEY, MG
NORTH, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (04): : 833 - 834
[3] NON-PROTEINOGENIC AMINO-ACID SYNTHESIS - SYNTHESIS OF BETA, GAMMA-UNSATURATED ALPHA-AMINO-ACIDS FROM ASPARTIC-ACID
BALDWIN, JE
MOLONEY, MG
NORTH, M
[J]. TETRAHEDRON, 1989, 45 (19) : 6319 - 6330
[4] NON-PROTEINOGENIC AMINO-ACID SYNTHESIS - THE BETA-ANION DERIVED FROM ASPARTIC-ACID, AND ITS APPLICATION TO ALPHA-AMINO-ACID SYNTHESIS
BALDWIN, JE
MOLONEY, MG
NORTH, M
[J]. TETRAHEDRON, 1989, 45 (19) : 6309 - 6318
[5] REGIOSELECTIVE FUNCTIONALIZATION OF CHIRAL NICKELACYCLES DERIVED FROM N-PROTECTED ASPARTIC AND GLUTAMIC ANHYDRIDES
CASTANO, AM
ECHAVARREN, AM
[J]. TETRAHEDRON LETTERS, 1990, 31 (33) : 4783 - 4786
[6] 1ST HYDROGEN ABSTRACTION REARRANGEMENT MODEL FOR THE COENZYME-B12-DEPENDENT METHYLMALONYL-COA TO SUCCINYL-COA CARBON SKELETON REARRANGEMENT REACTION
DOWD, P
WILK, B
WILK, BK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (20) : 7949 - 7951
[7] A MODEL FOR THE ENZYME-CATALYZED, COENZYME-B12-DEPENDENT INTERCONVERSION OF BETA-METHYLASPARTATE WITH GLUTAMATE
DOWD, P
CHOI, SC
DUAH, F
KAUFMAN, C
[J]. TETRAHEDRON, 1988, 44 (08) : 2137 - 2148
[8] STEREOCHEMISTRY OF CATABOLISM OF THE DNA-BASE THYMINE AND OF THE ANTI-CANCER DRUG 5-FLUOROURACIL
GANI, D
HITCHCOCK, PB
YOUNG, DW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (07): : 1363 - 1372
[9] PHERMONE SYNTHESIS .53. SYNTHESIS AND ABSOLUTE STEREOCHEMISTRY OF SERRICORNIN [(4S, 6S, 7S)-4,6-DIMETHYL-7-HYDROXY-3-NONANONE] - THE SEX-PHEROMONE OF THE CIGARETTE BEETLE
MORI, K
NOMI, H
CHUMAN, T
KOHNO, M
KATO, K
NOGUCHI, M
[J]. TETRAHEDRON, 1982, 38 (24) : 3705 - 3711
[10] TOTAL SYNTHESIS OF ADDA, THE UNIQUE C20 AMINO-ACID OF CYANOBACTERIAL HEPATOTOXINS
NAMIKOSHI, M
RINEHART, KL
DAHLEM, AM
BEASLEY, VR
CARMICHAEL, WW
[J]. TETRAHEDRON LETTERS, 1989, 30 (33) : 4349 - 4352

← 1 2 →