Pheromones via organoboranes. 2. Vinylic organoboranes. 8. Applications of the general stereoselective synthesis of (E)-disubstituted alkenes via thexylchloroborane …

HC Brown, HD Lee, SU Kulkarni

Index: Brown, Herbert C.; Lee, Hsiupu D.; Kulkarni, Surendra U. Journal of Organic Chemistry, 1986 , vol. 51, # 26 p. 5282 - 5286

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Citation Number: 16

Abstract

Various@)-pheromones of the general structures (E)-X-alken-1-yl acetates,(E)-X-alken-1- ols, and (E)-X-alken-1-als have been prepared via thexylchloroborane-dimethyl sulfide (ThxBHCl. SMe,). Hydroboration of acetate-funetionalized alkenes with ThxBHC1. SMez gives cleanly the corresponding thexylalkylchloroboranes (ThxBRCl, B). Hydridation of B with potassium triisopropoxyborohydride (KIPBH) at-78" C gives cleanly the ...

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