Intramolecular [4+ 3] cycloadditions-Stereochemical issues in the cycloaddition reactions of cyclopentenyl cations-A synthesis of (+)-dactylol

M Harmata, P Rashatasakhon…

文献索引：Harmata, Michael; Rashatasakhon, Paitoon; Barnes, Charles L. Canadian Journal of Chemistry, 2006 , vol. 84, # 10 p. 1456 - 1469

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被引用次数: 12

摘要

Five cyclopentanones were prepared for the purpose of examining the effects of stereogenic centers on the course of the intramolecular [4+ 3] cycloaddition reactions of cyclopentenyl cations. One substrate reacted with very high levels of diastereoselectivity and was converted to (+)-dactylol. The cyclopentenone without stereogenic centers on the tether or the five-membered ring gave two cycloadducts, the endo isomer being only slightly ...