2-phenyl isopropyl and t-butyl trichloroacetimidates: Useful reagents for ester preparation of N-protected amino acids under neutral conditions.

被引:42
作者
Thierry, J [1 ]
Yue, CW [1 ]
Potier, P [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
D O I
10.1016/S0040-4039(97)10851-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Phenylisopropyl and t-butyl trichloroacetamidates 1 and 2 are useful reagents for the esterification of N-protected aminoacids under mild neutral conditions. In the case of hydroxyl-containing amino acids, dialkylation occurs but no selectivity could be obtained. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1557 / 1560
页数:4
相关论文
共 10 条
[1]  
AMSTRONG A, 1988, TETRAHEDRON LETT, V29, P2483
[2]   FACILE SYNTHESIS OF TERT-BUTYL ESTER OF N-PROTECTED AMINO-ACIDS WITH TERT-BUTYL BROMIDE [J].
CHEVALLET, P ;
GARROUSTE, P ;
MALAWSKA, B ;
MARTINEZ, J .
TETRAHEDRON LETTERS, 1993, 34 (46) :7409-7412
[3]   BENZYL TRICHLOROACETIMIDATE, A VERSATILE REAGENT FOR ACID-CATALYZED BENZYLATION OF HYDROXY-GROUPS [J].
IVERSEN, T ;
BUNDLE, DR .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (23) :1240-1241
[4]   SYNTHETIC METHOD FOR N-BENZYLOXYCARBONYL HYDROXY AMINO-ACID TERT-BUTYL ESTERS [J].
KINOSHITA, H ;
ISHIKAWA, H ;
KOTAKE, H .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (10) :3111-3112
[5]  
Kokotos G, 1997, SYNTHESIS-STUTTGART, P168
[6]   MPM (4-METHOXYBENZYL) PROTECTION OF HYDROXY FUNCTIONS UNDER MILD ACIDIC CONDITIONS [J].
NAKAJIMA, N ;
HORITA, K ;
ABE, R ;
YONEMITSU, O .
TETRAHEDRON LETTERS, 1988, 29 (33) :4139-4142
[7]   NEW METHODS FOR THE SYNTHESIS OF GLYCOSIDES AND OLIGOSACCHARIDES - ARE THERE ALTERNATIVES TO THE KOENIGS-KNORR METHOD [J].
SCHMIDT, RR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (03) :212-235
[8]   ACID-CATALYZED BENZYLATION AND ALLYLATION BY ALKYL TRICHLOROACETIMIDATES [J].
WESSEL, HP ;
IVERSEN, T ;
BUNDLE, DR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11) :2247-2250
[9]  
WIDMER U, 1987, SYNTHESIS-STUTTGART, P568
[10]   2-PHENYL ISOPROPYL ESTERS AS CARBOXYL TERMINUS PROTECTING GROUPS IN THE FAST SYNTHESIS OF PEPTIDE-FRAGMENTS [J].
YUE, CW ;
THIERRY, J ;
POTIER, P .
TETRAHEDRON LETTERS, 1993, 34 (02) :323-326