α-amino esters as nucleophiles in diastereoselective palladium catalysed allylic substitution reactions

被引:21
作者
Humphries, ME
Clark, BP
Williams, JMJ
机构
[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
[2] Eli Lilly & Co, Lilly Res Ctr Ltd, Windlesham GU20 6PH, Surrey, England
关键词
D O I
10.1016/S0957-4166(98)00060-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Allylic acetates undergo palladium catalysed allylic substitution with amino ester nucleophiles. Using enantiomerically pure cx-amino esters, the substitution products are obtained with moderate diastereoselectivity (up to 85: 15: 70% d.e.). The reactions could also be performed using an enantiomerically pure ligand, which was found to exert a stronger influence over the stereochemical outcome. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:749 / 751
页数:3
相关论文
共 9 条
[1]   Palladium-catalysed asymmetric allylic substitution: Synthesis of alpha- and beta-amino acids [J].
Bower, JF ;
Jumnah, R ;
Williams, AC ;
Williams, JMJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (09) :1411-1420
[2]  
BURKHARDT U, 1997, ORGANOMETALLICS, V16, P5252
[3]   ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE TRANSITION-METAL COMPLEXES .8. PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC AMINATION [J].
HAYASHI, T ;
YAMAMOTO, A ;
ITO, Y ;
NISHIOKA, E ;
MIURA, H ;
YANAGI, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6301-6311
[4]   SYNTHESIS OF N-PROTECTED AMINO ESTERS VIA PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION [J].
JUMNAH, R ;
WILLIAMS, JMJ ;
WILLIAMS, AC .
TETRAHEDRON LETTERS, 1993, 34 (41) :6619-6622
[5]   PALLADIUM(0)-CATALYZED ALLYLIC ALKYLATION AND AMINATION OF ALLYLIC PHOSPHATES [J].
TANIGAWA, Y ;
NISHIMURA, K ;
KAWASAKI, A ;
MURAHASHI, SI .
TETRAHEDRON LETTERS, 1982, 23 (52) :5549-5552
[6]   ASYMMETRIC INDUCTION IN ALLYLIC ALKYLATIONS OF 3-(ACYLOXY)CYCLOALKENES [J].
TROST, BM ;
BUNT, RC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (09) :4089-4090
[7]   Synthesis and applications of a new class of phosphorus donor ligands for asymmetric catalysis [J].
Tye, H ;
Smyth, D ;
Eldred, C ;
Wills, M .
CHEMICAL COMMUNICATIONS, 1997, (11) :1053-1054
[8]   ENANTIOSELECTIVE ALLYLIC AMINATION WITH CHIRAL (PHOSPHINO-OXAZOLINE)PD CATALYSTS [J].
VONMATT, P ;
LOISELEUR, O ;
KOCH, G ;
PFALTZ, A ;
LEFEBER, C ;
FEUCHT, T ;
HELMCHEN, G .
TETRAHEDRON-ASYMMETRY, 1994, 5 (04) :573-584
[9]  
Williams JMJ, 1996, SYNLETT, P705