Stereoselective Double Lewis Acid/Organo-Catalyzed Dimerization of Donor-Acceptor Cyclopropanes into Substituted 2-Oxabicyclo[3.3.0]octanes

被引：34

作者：

Novikov, Roman A. ^{[1
,2
]}

Timofeev, Vladimir P. ^{[2
]}

Tomilov, Yury V. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia

[2] Russian Acad Sci, VA Engelhardt Mol Biol Inst, Moscow 119991, Russia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 14期

关键词：

HIGHLY DIASTEREOSELECTIVE SYNTHESIS; RING-OPENING REACTIONS; ACTIVATED CYCLOPROPANES; CYCLOADDITION REACTIONS; KHAYA-GRANDIFOLIOLA; ORGANIC-SYNTHESIS; FORMAL 3+2; ACID; DERIVATIVES; ALDEHYDES;

D O I：

10.1021/jo300720d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new approach for the dimerization of donor acceptor cyclopropanes (2-arylcyclopropane-1,1-dicarboxylates) under double-catalysis conditions by treatment with 20 mol % of GaCl3 and dimethyl 3,5-dimethyl-1-pyrazoline-3,5-dicarboxylate as a specific organocatalyst has been found. Under these conditions, the starting compounds are regio- and stereospecifically converted into polysubstituted 2-oxabicyclo[3.3.0]octanes. Two new rings, one C-O bond, and two C-C bonds are formed in this process, and four stereocenters are thus created. The reaction mechanism was thoroughly studied by NMR spectroscopy, and a number of intermediates were detected.

引用

页码：5993 / 6006

页数：14

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