Phosphine-catalyzed enantioselective [3+2] annulations of 2,3-butadienoates with imines

被引:120
作者
Jean, L [1 ]
Marinetti, A [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, UPR 2301, F-91198 Gif Sur Yvette, France
关键词
3+2] cycloadditions; enantioselective organocatalysis; phosphines; 3-pyrrolines;
D O I
10.1016/j.tetlet.2006.01.122
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first systematic screening of chiral phosphines in the cycloaddition reaction between 2,3-butadienoates and arylimines has led to the identification of fairly efficient catalysts. 2-Aryl-3-pyrrolines have been obtained with enantiomeric excesses up to 64%. In one instance, the enantiomeric excess could be increased to 91% ee by combining the enantioselective cyclization reaction with a crystallization step. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2141 / 2145
页数:5
相关论文
共 24 条
[1]   Asymmetric formation of quaternary carbon centers catalyzed by novel chiral 2,5-dialkyl-7-phenyl-7-phosphabicyclo[2.2.1]heptanes [J].
Chen, ZG ;
Zhu, GX ;
Jiang, QZ ;
Xiao, DM ;
Cao, P ;
Zhang, X .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (16) :5631-5635
[2]   INTRAMOLECULAR DIELS-ALDER REACTIONS IN ARYL ALLENECARBOXYLATES [J].
HIMBERT, G ;
FINK, D .
TETRAHEDRON LETTERS, 1985, 26 (36) :4363-4366
[3]  
Lang R. W., 1984, Org. Synth., V62, P202
[4]   Reactions of electron-deficient alkynes and allenes under phosphine catalysis [J].
Lu, XY ;
Zhang, CM ;
Xu, ZR .
ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (07) :535-544
[5]  
Marinetti A, 1999, SYNLETT, P1975
[6]  
Marinetti A, 2001, SYNTHESIS-STUTTGART, P2095
[7]   Nucleophilic phosphine organocatalysis [J].
Methot, JL ;
Roush, WR .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1035-1050
[8]   Ferrocenylphosphines as new catalysts for Baylis-Hillman reactions [J].
Pereira, SI ;
Adrio, J ;
Silva, AMS ;
Carretero, JC .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (24) :10175-10177
[9]   Chiral phosphine lewis bases catalyzed asymmetric aza-Baylis-Hiliman reaction of N-sulfonated imines with activated olefins [J].
Shi, M ;
Chen, LH ;
Li, CQ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) :3790-3800
[10]   DABCO-catalyzed reaction of allenic esters and ketones with salicyl N-tosylimines:: Synthesis of highly functionalized chromenes [J].
Shi, YL ;
Shi, M .
ORGANIC LETTERS, 2005, 7 (14) :3057-3060