Organocatalytic biomimetic reduction of conjugated nitroalkenes

被引：51

作者：

Zhang, Zhiguo ^{[1
]}

Schreiner, Peter R. ^{[1
]}

机构：

[1] Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany

来源：

SYNTHESIS-STUTTGART | 2007年 / 16期

关键词：

biomimetic reduction; Hantzsch ester; hydrogen bonding; nitroalkenes; thiourea;

D O I：

10.1055/s-2007-983805

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A thiourea-catalyzed biormimetic reduction of conjugated nitroalkenes has been developed. Various aromatic and aliphatic conjugated nitroalkenes can be reduced to give the respective nitroalkanes with good yields under mild conditions. This protocol is not only practical, but may also provide insight into the mechanisms of redox transformations in biological systems.

引用

页码：2559 / 2564

页数：6

共 50 条

[1] ROMPgel-supported tris(triphenylphosphine)rhodium(I) chloride:: a selective hydrogenation catalyst for parallel synthesis [J].

Årstad, E ;

Barrett, AGM ;

Tedeschi, L .

TETRAHEDRON LETTERS, 2003, 44 (13) :2703-2707

[2] SYNTHESIS OF ALPHA-MONOSUBSTITUTED INDOLES [J].

AUGUSTINE, RL ;

GUSTAVSE.AJ ;

WANAT, SF ;

PATTISON, IC ;

HOUGHTON, KS ;

KOLETAR, G .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (17) :3004-3011

[3] Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction) [J].

Ballini, R ;

Petrini, M .

TETRAHEDRON, 2004, 60 (05) :1017-1047

[4]

Berner OM, 2002, EUR J ORG CHEM, V2002, P1877

[5] Borrowing hydrogen: Indirect "Wittig" olerination for the formation of C-C bonds from alcohols [J].

Black, Phillip J. ;

Edwards, Michael G. ;

Williams, Jonathan M. J. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (19) :4367-4378

[6] INSITU GENERATION AND SYNTHETIC APPLICATION OF 2-PHENYLBENZIMIDAZOLINE TO THE SELECTIVE REDUCTION OF CARBON CARBON DOUBLE-BONDS OF ELECTRON-DEFICIENT OLEFINS [J].

CHIKASHITA, H ;

NISHIDA, S ;

MIYAZAKI, M ;

MORITA, Y ;

ITOH, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (02) :737-746

[7] Convenient catalytic, enantioselective conjugate reduction of nitroalkenes using CuF2 [J].

Czekelius, C ;

Carreira, EM .

ORGANIC LETTERS, 2004, 6 (24) :4575-4577

[8] Catalytic enantioselective conjugate reduction of β,β-disubstituted nitroalkenes [J].

Czekelius, C ;

Carreira, EM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (39) :4793-4795

[9] CHEMISTRY OF DIHYDROPYRIDINES [J].

EISNER, U ;

KUTHAN, J .

CHEMICAL REVIEWS, 1972, 72 (01) :1-+

[10] A HIGHLY CHEMOSELECTIVE REDUCTION OF CONJUGATED NITRO OLEFINS WITH HANTZSCH ESTER IN THE PRESENCE OF SILICA-GEL [J].

FUJII, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (11) :4029-4035

← 1 2 3 4 5 →