Investigations into the enantioselective C-protonation of prostereogenic enolate(s) derived from N,N′-diisopropyl-2-phenylpropanamide using suicide C-based proton sources

被引：12
作者：
Coumbarides, GS [1 ]
Eames, J [1 ]
Ghilagaber, S [1 ]
Suggate, MJ [1 ]
机构：
[1] Queen Mary Univ London, Dept Chem, London E1 4NS, England
来源：
TETRAHEDRON LETTERS | 2004年 / 45卷 / 51期
基金：
英国工程与自然科学研究理事会;
关键词：
D O I：
10.1016/j.tetlet.2004.10.090
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of enantionterically enriched (-)-(R)-N, N'-diisopropyl-2-phenylpropanamide was achieved in up to 69'Yo enantionteric excess by symmetrisation of the corresponding racemic amide by addition of sec-BuLi (to give the corresponding achiral lithium enolate) and subsequent desymmetrisation by the addition of a chiral C-based proton source. We discuss potential factors that may be responsible for this observed enantioselectivity and comment on the role of the chiral acid. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：9469 / 9474
页数：6
相关论文
共 64 条
[11]   ENANTIOSELECTIVITY IN ENEDIOL-HYDROXYKETONE TAUTOMERIZATION [J].
DUHAMEL, L ;
LAUNAY, JC .
TETRAHEDRON LETTERS, 1983, 24 (39) :4209-4212
[12]   DE-RACEMIZATION BY ENANTIOSELECTIVE PROTONATION - NEW METHOD FOR ENANTIOMERIC ENRICHMENT OF ALPHA-AMINO-ACIDS [J].
DUHAMEL, L ;
PLAQUEVENT, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (23) :7415-7416
[13]   ENANTIOSELECTIVE ELECTROPHILIC BOND CONSTRUCTION TO THE ALPHA-CARBON OF ALPHA-AMINOACIDS [J].
DUHAMEL, L ;
DUHAMEL, P ;
FOUQUAY, S ;
EDDINE, J ;
PESCHARD, O ;
PLAQUEVENT, JC ;
RAVARD, A ;
SOLLIARD, R ;
VALNOT, JY ;
VINCENS, H .
TETRAHEDRON, 1988, 44 (17) :5495-5506
[14]  
DUHAMEL L, 1982, B SOC CHIM FR
[15]   Diastereoselective protonation of chiral enolates derived from 2,4-dimethyl-1-tetralone using carbonyl chelating proton donors [J].
Eames, J .
TETRAHEDRON LETTERS, 1999, 40 (31) :5787-5790
[16]   Investigations into the enantioselective protonation of enolates derived from 2-methyl-1-tetralone using a chiral diamine ligand [J].
Eames, J ;
Weerasooriya, N .
TETRAHEDRON LETTERS, 2000, 41 (04) :521-523
[17]  
Eames J, 1999, CHIRALITY, V11, P787, DOI 10.1002/(SICI)1520-636X(1999)11:10<787::AID-CHIR8>3.0.CO
[18]  
2-0
[19]   Recent advances into the enantioselective protonation of prostereogenic enol derivatives [J].
Eames, J ;
Weerasooriya, N .
TETRAHEDRON-ASYMMETRY, 2001, 12 (01) :1-24
[20]   PROTON TRANSFER ACID-BASE CATALYSIS + ENZYMATIC HYDROLYSIS .I. ELEMENTARY PROCESSES [J].
EIGEN, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1964, 3 (01) :1-&
1234567