The Journal of Organic Chemistry

Regioselective synthesis of trimethylsilyl-substituted. alpha.-allenic alcohols via propargylic organoboranes

KK Wang, SS Nikam, CD Ho

Index: Wang, Kung K.; Nikam, Sham S.; Ho, Chihmei D. Journal of Organic Chemistry, 1983 , vol. 48, # 26 p. 5376 - 5377

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Citation Number: 31

Abstract

35 min) followed by the addition of 4/3 equiv of BF,-OEt,(0" C, 15 min) 3 provided the corresponding propargylic organoborane 3. To the reaction mixture were then added aldehydes or ketones (room temperature, 1.5 h), which on oxidative workup gave the corresponding trimethylsilylsubstituted a-allenic alcohols 5 in excellent isolated yields (Table I). None of the corresponding@-acetylenic alcohols were dete~ ted.~ The reactions ...