Studies directed toward the synthesis of prostaglandins. Useful boron-mediated olefin syntheses

DA Evans, TC Crawford, RC Thomas…

Index: Evans,D.A. et al. Journal of Organic Chemistry, 1976 , vol. 41, p. 3947 - 3953

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Citation Number: 48

Abstract

The reactions of bis (2-ethylcyclopentyl) borane, dicyclopentylborane, with 3-(tert- butydimethylsiloxy)-1-octyne and subsequent iodine-promoted rearrangement to 2 olefins or unsymmetrical acetylenes are reported. Mixed dialkylboranes are also examined in this olefin-acetylene cross process. Significant amounts of thexyl-migrated acetylenic by- products are observed in several instances. The synthesis of either E-or 2-1, 2- ...