Efficient synthesis of β2-amino acid by homologation of α-amino acids involving the Reformatsky reaction and Mannich-type imminium electrophile

被引:77
作者
Moumne, R
Lavielle, S
Karoyan, P
机构
[1] Univ Paris 06, CNRS, UMR 7613, F-75252 Paris 05, France
[2] Senn Chem AG, CH-8157 Dielsdorf, Switzerland
关键词
D O I
10.1021/jo060316a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Development of new methods for the synthesis of P-amino acids is important as polymers of these compounds are promising peptidomimetic candidates in medicinal chemistry. We report here our findings on a new and highly efficient general strategy for the synthesis of beta(2)-amino acids by homologation of a.-amino acids, involving the Reformatsky reaction and Mannich-type imminium electrophile.
引用
收藏
页码:3332 / 3334
页数:3
相关论文
共 43 条
[1]  
ANWER MK, 1980, SYNTHESIS-STUTTGART, P929
[2]  
ARANATIS TE, 1998, J CHEM SOC P1, P521
[3]  
BEDOW JE, 2004, J CHEM SOC CHEM COMM, P2778
[4]  
Böhm A, 2000, HELV CHIM ACTA, V83, P3262, DOI 10.1002/1522-2675(20001220)83:12<3262::AID-HLCA3262>3.0.CO
[5]  
2-P
[6]   β-peptides:: From structure to function [J].
Cheng, RP ;
Gellman, SH ;
DeGrado, WF .
CHEMICAL REVIEWS, 2001, 101 (10) :3219-3232
[7]  
DARDOIZE F, 1973, B SOC CHIM FR II-CH, P1668
[8]   Highly enantioselective conjugate addition of dialkylzinc reagents to acyclic nitroalkenes:: A catalytic route to β2-amino acids, aldehydes, and alcohols [J].
Duursma, A ;
Minnaard, AJ ;
Feringa, BL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (13) :3700-3701
[9]   Synthesis of N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-protected (Fmoc) β-amino acids (= homo-α-amino acids) by direct homologation [J].
Ellmerer-Müller, EP ;
Brössner, D ;
Maslouh, N ;
Takó, A .
HELVETICA CHIMICA ACTA, 1998, 81 (01) :59-65
[10]   NEW PROCEDURE FOR THE DIRECT GENERATION OF TITANIUM ENOLATES - DIASTEREOSELECTIVE BOND CONSTRUCTIONS WITH REPRESENTATIVE ELECTROPHILES [J].
EVANS, DA ;
URPI, F ;
SOMERS, TC ;
CLARK, JS ;
BILODEAU, MT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8215-8216