Cyclopropanation with Fischer acyloxycarbene complexes:: Preparation of cyclopropane and cycloheptane-fused γ-lactones

被引：23

作者：

Barluenga, J ^{[1
]}

Aznar, F ^{[1
]}

Gutiérrez, I ^{[1
]}

Martín, JA ^{[1
]}

机构：

[1] Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, Unidad CSIC, E-33071 Oviedo, Spain

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 16期

关键词：

D O I：

10.1021/ol026225r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A sequential acylation-intramolecular cyclopropanation reaction takes place upon treatment of a series of tetraalkylammonium acylchromates with beta,gamma-unsaturated acyl chlorides at -10 degreesC. The reaction leads to 2-oxabicyclo[3.1.0]hexan-3-ones with exo selectivity in good yields. The diastereoselectivity of the reaction allows the preparation of cis-divinyl cyclopropanes, which evolve via Cope sigmatropic reaction toward cycloheptadiene derivatives. Furthermore, the aromatic Cope rearrangement of a series of cis-aryl vinyl cyclopropanes prepared by means of this methodology has been studied.

引用

页码：2719 / 2722

页数：4

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