ZINC MEDIATED ADDITION OF ACTIVE HALIDES TO A GLYCINE CATION EQUIVALENT - SYNTHESIS OF N-BOC-L-PROPARGYLGLYCINE

被引:11
作者
ABOOD, NA
NOSAL, R
机构
[1] Department of Chemistry Searle Research and Development, Skokie
关键词
D O I
10.1016/S0040-4039(00)73067-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of allylic, benzylic and propargylic halides with zinc in the presence of the glycine cation equivalent, methyl N-Boc-2-acetoxyglycine, affords Boc protected amino acid derivatives in high yield. Resolution of methyl N-Boc-propargylglycine with alpha-chymotrypsin affords N-Boc-L-propargylglycine in 99% e.e..
引用
收藏
页码:3669 / 3672
页数:4
相关论文
共 16 条
[1]   SYNTHESIS OF N-SUBSTITUTED AZIRIDINE-2-CARBOXYLATES [J].
BERNSTEIN, Z ;
BENISHAI, D .
TETRAHEDRON, 1977, 33 (08) :881-883
[2]   NEW SYNTHESES OF ALPHA-AMINO-ACIDS BASED ON N-ACYLIMINO ACETATES [J].
BRETSCHNEIDER, T ;
MILTZ, W ;
MUNSTER, P ;
STEGLICH, W .
TETRAHEDRON, 1988, 44 (17) :5403-5414
[3]   REACTIONS OF AN ELECTROPHILIC GLYCINE CATION EQUIVALENT WITH GRIGNARD-REAGENTS - A SIMPLE SYNTHESIS OF BETA,GAMMA-UNSATURATED AMINO-ACIDS [J].
CASTELHANO, AL ;
HORNE, S ;
BILLEDEAU, R ;
KRANTZ, A .
TETRAHEDRON LETTERS, 1986, 27 (22) :2435-2438
[4]  
EMERT P, 1988, TETRAHEDRON LETT, V29, P1265
[5]  
GRESHON H, 1949, J AM CHEM SOC, V71, P3574
[6]   THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS VIA THE ADDITION OF GRIGNARD-REAGENTS TO IMINE DERIVATIVES [J].
HAMON, DPG ;
MASSYWESTROPP, RA ;
RAZZINO, P .
TETRAHEDRON, 1992, 48 (24) :5163-5178
[7]   ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS BY ALKYLATION OF N-[N-BIS-(METHYLTHIO)METHYLENEGLYCYL]-2,5-BIS(METHOXYMETHOXYMETHYL)PYRROLIDINE AND ENANTIOSELECTIVE SYNTHESIS OF PROTECTED (2S,9S)-2-AMINO-8-OXO-9,10-EPOXYDECANOIC ACID [J].
IKEGAMI, S ;
UCHIYAMA, H ;
HAYAMA, T ;
KATSUKI, T ;
YAMAGUCHI, M .
TETRAHEDRON, 1988, 44 (17) :5333-5342
[8]   SYNTHESIS OF DIASTEREO- AND ENANTIOMERICALLY PURE ALPHA-AMINO-GAMMA-OXO ACID ESTERS BY REACTION OF ACYLIMINOACETATES WITH ENAMINES DERIVED FROM 6-MEMBERED KETONES [J].
KOBER, R ;
PAPADOPOULOS, K ;
MILTZ, W ;
ENDERS, D ;
STEGLICH, W ;
REUTER, H ;
PUFF, H .
TETRAHEDRON, 1985, 41 (09) :1693-1701
[9]   SYNTHESIS OF L-PROPARGYLGLYCINE AND DERIVATIVES [J].
LEUKART, O ;
CAVIEZEL, M ;
EBERLE, A ;
ESCHER, E ;
TUNKYI, A ;
SCHWYZER, R .
HELVETICA CHIMICA ACTA, 1976, 59 (06) :2181-2183
[10]   SYNTHESIS OF GAMMA,DELTA-UNSATURATED ALPHA-AMINO-ACIDS FROM ALLYLSILANES AND GLYCIDYL CATION EQUIVALENTS [J].
MOOIWEER, HH ;
HIEMSTRA, H ;
SPECKAMP, WN .
TETRAHEDRON, 1989, 45 (14) :4627-4636