Tetrahedron

Photoinduced vinylcyclopropane-cyclopentene rearrangement: A methodology for chiral bicyclo [3.2. 0] heptenes. Formai syntheses of (±)-grandisol and naturally …

HR Sonawane, VG Naik, NS Bellur, VG Shah…

文献索引：Sonawane, Harikisan R.; Naik, Vishwaniyant G.; Bellur, Nanjundiah S.; Shah, Virendra G.; Purohit, Pramod C.; et al. Tetrahedron, 1991 , vol. 47, # 38 p. 8259 - 8276

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被引用次数: 14

摘要

The problem of achieving reaction selectivity in cis-alkyl vinylcyclopropanes in favour of their rearrangement to cyclopentenes, obviating the competing low energy process of the [1, 5](homo) sigmatropic hydrogen shift, is addressed. It has been demonstrated that the readily available bicyclo [4.1. 0] heptenes derived from (+)-Δ3-carene.(1), upon photosensitized irradiation, are conveniently transformed into chiral cis-bicyclo [3.2. 0] heptenes. The ...