Stereoselective Michael addition reactions of 5-glyco-4-nitrocyclohex-1-enes

被引：21

作者：

Areces, P

Gil, MV

Higes, FJ

Román, E ^{[1
]}

Serrano, JA

机构：

[1] Univ Extremadura, Dept Quim Organ, Fac Ciencias, E-06071 Badajoz, Spain

[2] Univ Extremadura, Dept Quim Inorgan, Fac Ciencias, E-06071 Badajoz, Spain

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 46期

关键词：

Michael reactions; nitro compounds; stereoselectivity; cyclohexenes;

D O I：

10.1016/S0040-4039(98)01911-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Michael additions of 5-glyco-4-nitrocyclohex-1-enes (2 and 3) proceeded in a stereoselective way, leading in each case to single adducts in which the electron-deficient alkenes add on the C-4 of the cyclohexene rings, in a trans mode to the adjacent, sterically demanding, sugar side-chain. When dimethyl maleate or dimethyl fumarate and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were used, there was in situ elimination of nitrous acid, and the product consisted in a 1:1 mixture of the epimeric alpha,beta-unsaturated esters 7. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：8557 / 8560

页数：4

共 9 条

[1] Baer H.H., 1970, CHEM NITRO NITROSO 2, P75
[2] MICHAEL ADDITION OF NITROALKANES TO DIMETHYL MALEATE WITH DBU - A NEW DIRECT METHOD FOR THE SYNTHESIS OF POLYFUNCTIONALIZED ALPHA,BETA-UNSATURATED ESTERS
BALLINI, R
RINALDI, A
[J]. TETRAHEDRON LETTERS, 1994, 35 (49) : 9247 - 9250
[3] Bergmann E.D., 1959, ORG REACTIONS, V10, P179
[4] FRISCH MJ, 1995, GAUSSIAN 9J
[5] ENANTIOSELECTIVE SYNTHESIS OF CYCLOHEXENE NITROALDEHYDES
MORENO, MC
PLUMET, J
ROMAN, E
SERRANO, JA
RODRIGUEZ, ML
RUIZPEREZ, C
[J]. TETRAHEDRON LETTERS, 1989, 30 (24) : 3179 - 3182
[6] OARE DA, 1989, TOP STEREOCHEM, V19, P227
[7] Schmalz H.-G., 1991, COMPREHENSIVE ORGANI, V4, P199
[8] SEEBACH D, 1979, CHIMIA, V33, P1
[9] ENANTIOSELECTIVE SYNTHESIS OF CYCLOHEXENE NITRO ALDEHYDES VIA DIELS-ALDER REACTIONS WITH SUGAR NITROOLEFINS
SERRANO, JA
MORENO, MC
ROMAN, E
ARJONA, O
PLUMET, J
JIMENEZ, J
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (12): : 3207 - 3212

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