High pressure activation in the asymmetric Michael addition of chiral imines to alkyl and aryl crotonates

被引:32
作者
Camara, C
Joseph, D
Dumas, F
d'Angelo, J
Chiaroni, A
机构
[1] Univ Paris Sud, Ctr Etud Pharmaceut, CNRS, Unite Chim Organ Associee, F-92296 Chatenay Malabry, France
[2] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
diastereoselection; enantioselection; imines; Michael reaction; pressure; reactions under;
D O I
10.1016/S0040-4039(02)00054-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
High pressure-mediated Michael addition of chiral imines derived from 2-methylcyclopentanone, 2-methylcyclohexanone and optically active 1-phenylethylamine, to methyl and phenyl crotonates as investigated, The corresponding adducts ere obtained in fair yields and with a high degree of regio-, diastereo- and enantioselectivity. (C) 2002 Else vier Science Ltd. All rights reserved.
引用
收藏
页码:1445 / 1448
页数:4
相关论文
共 34 条
[1]   ASYMMETRIC BRIDGING ANNULATION REACTION INVOLVING THE INTRAMOLECULAR CONJUGATE ADDITION OF CHIRAL IMINES TO ENOATES - ACCESS TO A POLYCYCLIC SYSTEM RELATED TO THE TAXANE CORE [J].
CAVE, C ;
BOGGERO, S ;
CASAS, R ;
DUMAS, F ;
MAHUTEAU, J ;
DANGELO, J .
TETRAHEDRON-ASYMMETRY, 1995, 6 (11) :2647-2650
[2]   Condensation of chiral imines and chiral beta-enaminoesters with maleic and citraconic anhydrides [J].
Cave, C ;
Gassama, A ;
Mahuteau, J ;
dAngelo, J ;
Riche, C .
TETRAHEDRON LETTERS, 1997, 38 (27) :4773-4776
[3]   Stereochemical aspects in the asymmetric Michael addition of chiral imines to substituted electrophilic alkenes [J].
Cave, C ;
Desmaele, D ;
dAngelo, J ;
Riche, C ;
Chiaroni, A .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (13) :4361-4368
[4]   6-allyl-8,8-dimethyl-3-oxo-2-(1-phenylethyl)-2-azabicyclo[4.3.0]non-1(9)-ene-5-carboxylic acid, a key compound in the asymmetric synthesis of quadrone [J].
Chiaroni, A ;
Riche, C ;
Francoise, D ;
Mauduit, M ;
Miet, C .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1998, 54 :401-403
[5]  
Ciobanu M, 1997, LIEBIGS ANN-RECL, P623
[6]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO
[7]  
2-V
[8]   Enantioselective access to five- and six-membered nitrogen-containing heterocycles, based on the asymmetric Michael addition of chiral imines and chiral enamino esters [J].
d'Angelo, J ;
Cave, C ;
Desmaele, D ;
Gassama, A ;
Thominiaux, C ;
Riche, C .
HETEROCYCLES, 1998, 47 (02) :725-746
[9]   AN EFFICIENT ASYMMETRIC SPIROANNULATION PROCESS [J].
DANGELO, J ;
FERROUD, C ;
RICHE, C ;
CHIARONI, A .
TETRAHEDRON LETTERS, 1989, 30 (47) :6511-6514
[10]   THE ASYMMETRIC MICHAEL ADDITION PROCESS INVOLVING CHIRAL IMINES - STEREOCHEMICAL DATA IN SUPPORT OF A CYCLIC-LIKE TRANSITION-STATE [J].
DANGELO, J ;
GUINGANT, A ;
RICHE, C ;
CHIARONI, A .
TETRAHEDRON LETTERS, 1988, 29 (22) :2667-2670