A chiral relay auxiliary for the synthesis of homochiral α-amino acids

被引:67
作者
Bull, SD
Davies, SG
Epstein, SW
Leech, MA
Ouzman, JVA
机构
[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England
[2] Univ Oxford, Chem Crystallog Lab, Oxford OX1 3PD, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 15期
关键词
D O I
10.1039/a803124j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new chiral auxiliary (3S)-N,N'-bis(p-methoxybenzyl)-3-isopropylpiperazine-2,5-dione 7 has been developed for the asymmetric synthesis of a-amino acids. The auxiliary 7 employs a novel chiral relay network based on non-stereogenic N-benzyl protecting groups which enhance the diastereoselectivity observed during alkylation of its C-6 enolate 25.
引用
收藏
页码:2321 / 2330
页数:10
相关论文
共 48 条
[11]   WEIGHTING SCHEME FOR LEAST-SQUARES STRUCTURE REFINEMENT [J].
CARRUTHERS, JR ;
WATKIN, DJ .
ACTA CRYSTALLOGRAPHICA SECTION A, 1979, 35 (JUL) :698-699
[12]   METHYLENE PIPERAZINE-2,5-DIONES AS TEMPLATES FOR THE SYNTHESIS OF AMINO-ACID DERIVATIVES [J].
CHAI, CLL ;
KING, AR .
TETRAHEDRON LETTERS, 1995, 36 (24) :4295-4298
[13]   PROBING PROTEIN-STRUCTURE AND FUNCTION WITH AN EXPANDED GENETIC-CODE [J].
CORNISH, VW ;
MENDEL, D ;
SCHULTZ, PG .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (06) :621-633
[14]  
DArrigo MC, 1995, J CHEM RES-S, P430
[15]  
DARRIGO MC, 1995, J CHEM RES-S, P162
[16]  
DAVIES JS, 1985, AMINO ACIDS PEPTIDES
[17]  
DUTHALER RO, 1994, TETRAHEDRON, V50, P1540
[18]   ASYMMETRIC GLYCINE ENOLATE ALDOL REACTIONS - SYNTHESIS OF CYCLOSPORINES UNUSUAL AMINO-ACID, MEBMT [J].
EVANS, DA ;
WEBER, AE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (21) :6757-6761
[19]   Ruthenium(II) in ring closing metathesis for the stereoselective preparation of cyclic 1-amino-1-carboxylic acids. [J].
Hammer, K ;
Undheim, K .
TETRAHEDRON, 1997, 53 (06) :2309-2322
[20]  
KAMPHIUS J, 1990, BIOPROCESS APPL ENZY, V42