Microwave activation of an asymmetric Michael reaction:: unexpected behaviour of chiral α-alkoxy imines

被引:13
作者
Camara, C [1 ]
Keller, L [1 ]
Dumas, F [1 ]
机构
[1] Univ Paris Sud, Ctr Etudes Pharmaceut, CNRS, Unite Assoc,BIOCIS, F-92290 Chatenay Malabry, France
关键词
D O I
10.1016/S0957-4166(03)00573-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
While it has been previously established that chiral alpha-alkoxy imines undergo thermal rearrangement at temperatures above 50degreesC, the microwave activation of the Michael addition between chiral imine 3b and methyl acrylate at 100degreesC led cleanly to the corresponding Michael adduct 5b without the formation of any rearranged product and with the same regio- and stereoselectivity as the corresponding thermal condensation at 40degreesC (ee 95%). (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3263 / 3266
页数:4
相关论文
共 33 条
[1]  
ABENHAIM D, 1994, HETEROCYCLES, V38, P793
[2]  
[Anonymous], [No title captured]
[3]   A NEW REACTION VESSEL FOR ACCELERATED SYNTHESES USING MICROWAVE DIELECTRIC SUPER-HEATING EFFECTS [J].
BAGHURST, DR ;
MINGOS, DMP .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1992, (07) :1151-1155
[4]   Diastereoselective α-iminoamine rearrangement:: asymmetric synthesis of (R)-(-)- and (S)-(+)-2-benzyl-2-hydroxycyclohexanone [J].
Bisel, P ;
Lauktien, G ;
Weckert, E ;
Frahm, AW .
TETRAHEDRON-ASYMMETRY, 1998, 9 (22) :4027-4034
[5]  
CAMARA C, 2003, THESIS U PARIS SUD
[6]   THE ASYMMETRIC MICHAEL ADDITION-REACTIONS USING CHIRAL IMINES [J].
DANGELO, J ;
DESMAELE, D ;
DUMAS, F ;
GUINGANT, A .
TETRAHEDRON-ASYMMETRY, 1992, 3 (04) :459-505
[7]  
DANGELO J, Patent No. 0017281
[8]   The origin of the stereoselectivity in the asymmetric Michael reaction using chiral imines secondary enamines under neutral conditions: a computational investigation [J].
Dau, METH ;
Riche, C ;
Dumas, F ;
d'Angelo, J .
TETRAHEDRON-ASYMMETRY, 1998, 9 (06) :1059-1064
[9]   Microwave-mediated selective monotetrahydropyranylation of symmetrical diols catalyzed by iodine [J].
Deka, N ;
Sarma, JC .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (06) :1947-1948
[10]   A FACILE CLAISEN REARRANGEMENT INVOLVING THE TRANSIENT TAUTOMERIC ENAMINE FORMS OF ALPHA-ALLYLOXYIMINES AND ALPHA-PROPARGYLOXYIMINES [J].
DESMAELE, D ;
CHAMPION, N .
TETRAHEDRON LETTERS, 1992, 33 (31) :4447-4450