Efficient Stereoselective Synthesis of Nitrocyclopropanes by the Oxidative Cyclization of Michael Adducts of Nitroolefins with Activated Methylene Compounds

被引：56

作者：

Fan, Renhua ^{[1
]}

Ye, Yang ^{[1
]}

Li, Weixun ^{[1
]}

Wang, Lingfei ^{[1
]}

机构：

[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 16期

关键词：

cyclization; cyclopropanes; hypervalent compounds; Michael addition; oxidation; stereoselectivity;

D O I：

10.1002/adsc.200800452

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient oxidative cyclopropanation of the Michael adducts of nitroolefins with activated methylene compounds by the combination of iodobenzene diacetate and tetrabutylammonium iodide is reported. Highly functionalized nitrocyclopropanes are synthesized in moderate to good yields via the Michael addition and cyclopropanation with high diastereoselectivity and enantioselectivity under mild conditions.

引用

页码：2488 / 2492

页数：5

共 94 条

[1] Asymmetric sulfonium ylide mediated cyclopropanation: Stereocontrolled synthesis of (+)-LY354740 [J].

Aggarwal, VK ;

Grange, E .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (02) :568-575

[2] Catalytic cyclopropanation of electron deficient alkenes mediated by chiral and achiral sulfides: scope and limitations in reactions involving phenyldiazomethane and ethyl diazoacetate [J].

Aggarwal, VK ;

Smith, HW ;

Hynd, G ;

Jones, RVH ;

Fieldhouse, R ;

Spey, SE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (19) :3267-3276

[3]

Aggarwal VK, 2001, ANGEW CHEM INT EDIT, V40, P1433, DOI 10.1002/1521-3773(20010417)40:8<1433::AID-ANIE1433>3.0.CO

[4]

2-E

[5] Catalytic asymmetric Diels-Alder reactions of α-thioacrylates for the preparation of norbornenone [J].

Aggarwal, VK ;

Anderson, ES ;

Jones, DE ;

Obierey, KB ;

Giles, R .

CHEMICAL COMMUNICATIONS, 1998, (18) :1985-1986

[6] Asymmetric cyclopropanation reaction under phase-transfer catalyzed conditions [J].

Arai, S ;

Nakayama, K ;

Ishida, T ;

Shioiri, T .

TETRAHEDRON LETTERS, 1999, 40 (22) :4215-4218

[7] REACTIONS OF CONJUGATED NITRO OLEFINS WITH PHOSPHORANES AND WITH DIMETHYLSULFOXONIUM METHYLIDE TO GIVE YLIDES AND NITROCYCLOPROPANES RESPECTIVELY [J].

ASUNSKIS, J ;

SHECHTER, H .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (03) :1164-&

[8] REACTIONS OF NITRO SUGARS .46. NUCLEOPHILIC RING-OPENING IN A CARBOHYDRATE NITROCYCLOPROPANE - A STEREOSPECIFIC APPROACH TO CHIRAL ISOALKYL STRUCTURES [J].

BAER, HH ;

WILLIAMS, U ;

RADATUS, B .

CARBOHYDRATE RESEARCH, 1988, 174 :291-303

[9] A general procedure for the one-pot preparation of polyfunctionalized nitrocyclopropanes [J].

Ballini, R ;

Fiorini, D ;

Palmieri, A .

SYNLETT, 2003, (11) :1704-1706

[10] Development of a catalytic enantioselective conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes for the synthesis of endothelin-A antagonist ABT-546. Scope, mechanism, and further application to the synthesis of the antidepressant rolipram [J].

Barnes, DM ;

Ji, JG ;

Fickes, MG ;

Fitzgerald, MA ;

King, SA ;

Morton, HE ;

Plagge, FA ;

Preskill, M ;

Wagaw, SH ;

Wittenberger, SJ ;

Zhang, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) :13097-13105

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