Stereoselective preparation of (E)-ε-nitro-β,γ-unsaturated methyl esters:: Amberlyst A 27, using microwave, as superior catalyst for the 1,6-conjugate addition of nitroalkanes to methyl 1,3-butadiene-1-carboxylate

被引：25

作者：

Ballini, R ^{[1
]}

Bosica, G ^{[1
]}

Fiorini, D ^{[1
]}

机构：

[1] Univ Camerino, Dipartimento Sci Chim, I-62032 Camerino, MC, Italy

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 48期

关键词：

nitroalkanes; conjugate addition; microwave; catalysis; stereoselective;

D O I：

10.1016/S0040-4039(01)01843-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,6-Conjugate addition of nitroalkanes to methyl 1,3-b-atadiene-1-carboxylate, performed with Amberlyst A 27, using microwaves and in the absence of any solvent, allows the prevalent formation of the beta,gamma -unsaturated adduct, over the alpha,beta -unsaturated one. The products were exclusively obtained as (E)-isomers. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：8471 / 8473

页数：3

共 17 条

[1] Amberlyst A-27, an efficient heterogeneous catalyst for the Michael reaction of nitroalkanes with beta-substituted alkene acceptors
Ballini, R
Marziali, P
Mozzicafreddo, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09) : 3209 - 3211
[2] Ballini R, 1998, EUR J ORG CHEM, V1998, P355, DOI 10.1002/(SICI)1099-0690(199802)1998:2<355::AID-EJOC355>3.0.CO
[3] 2-2
[4] Ballini R, 1997, RRD ORG CHEM, V1, P11
[5] 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
[6] Ballini R, 1997, STUD NAT PROD CHEM, V19, P117
[7] The Michael reaction of nitroalkanes with conjugated enones in aqueous media
Ballini, R
Bosica, G
[J]. TETRAHEDRON LETTERS, 1996, 37 (44) : 8027 - 8030
[8] BALLINI R, 1987, SYNTHESIS-STUTTGART, P711
[9] A CONVERSION OF CHOLEST-4-EN-3-ONE INTO CHOLESTEROL
BIRCH, AJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1950, (SEP): : 2325 - 2326
[10] MICROWAVE-ASSISTED ORGANIC-REACTIONS
CADDICK, S
[J]. TETRAHEDRON, 1995, 51 (38) : 10403 - 10432

← 1 2 →