One-pot synthesis of γ-diketones, γ-keto esters, and conjugated cyclopentenones from nitroalkanes

被引：37

作者：

Ballini, R ^{[1
]}

Barboni, L ^{[1
]}

Bosica, G ^{[1
]}

Fiorini, D ^{[1
]}

机构：

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

来源：

SYNTHESIS-STUTTGART | 2002年 / 18期

关键词：

nitroalkanes; gamma-diketones; gamma-keto esters; cyclopentenones; DBU;

D O I：

10.1055/s-2002-35993

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conjugated addition of primary nitroalkanes to alpha,beta-unsaturated ketones or alpha,beta-unsaturated esters, in the presence of two equivalents of DBU, allows the one-pot prepration of gamma-diketones or gamma-keto esters, respectively. When 2-aryl-1-nitroethane derivatives are employed as starting nitroalkanes in the reaction with alpha.beta-unsaturated ketones, the one-pot formation of cyclopentenones is observed.

引用

页码：2725 / 2728

页数：4

共 29 条

[1] An expeditious synthesis of (±)-desepoxy-4,5-didehydromethylenomycin A methyl ester
Balczewski, P
Mikolajczyk, M
[J]. ORGANIC LETTERS, 2000, 2 (08) : 1153 - 1155
[2] Michael addition of nitroalkanes to dimethyl citraconate, with DBU as base: An unexpected, one-pot synthesis of polyfunctionalized carbonyl derivatives
Ballini, R
Barboni, L
Bosica, G
Fiorini, D
Gil, MV
[J]. SYNLETT, 2002, (10) : 1706 - 1708
[3] Unprecedented, selective Nef reaction of secondary nitroalkanes promoted by DBU under basic homogeneous conditions
Ballini, R
Bosica, G
Fiorini, D
Petrini, M
[J]. TETRAHEDRON LETTERS, 2002, 43 (30) : 5233 - 5235
[4] Ballini R, 1997, RRD ORG CHEM, V1, P11
[5] BOSSARD P, 1986, ADV HETEROCYCL CHEM, V30, P384
[6] A FACILE AND GENERAL ENTRY TO OPTICALLY-ACTIVE PHEROMONES AND AROMAS WITH GAMMA-ALKYL-GAMMA-LACTONE STRUCTURES - A STUDY OF SOME LACTONE DERIVATIVES OF PENTOSES
CARDELLACH, J
FONT, J
ORTUNO, RM
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (02) : 327 - 331
[7] SYNTHESIS OF THERAPEUTICALLY USEFUL PROSTAGLANDIN AND PROSTACYCLIN ANALOGS
COLLINS, PW
DJURIC, SW
[J]. CHEMICAL REVIEWS, 1993, 93 (04) : 1533 - 1564
[8] RECENT ADVANCES IN FURAN CHEMISTRY .1.
DEAN, FM
[J]. ADVANCES IN HETEROCYCLIC CHEMISTRY, 1982, 30 : 167 - 238
[9] ELLISON RA, 1973, SYNTHESIS-STUTTGART, P397
[10] STEREOSELECTIVE REDUCTION OF GAMMA-OXOBUTANOIC ACIDS USING DIBAL-H AND ZNCL2
FRENETTE, R
MONETTE, M
BERNSTEIN, MA
YOUNG, RN
VERHOEVEN, TR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) : 3083 - 3089

← 1 2 3 →