Vinylic organoboranes. 6. A general synthesis of (E)-disubstituted-alkenes or ketones via the (E)-(1-substituted-1-alkenyl) boronic esters

HC Brown, D Basavaiah, SU Kulkarni…

Index: Brown, Herbert C.; Basavaiah, D.; Kulkarni, Surendra U.; Lee, Hsiupu D.; Negishi, Ei-ichi; Katz, Jean-Jacques Journal of Organic Chemistry, 1986 , vol. 51, # 26 p. 5270 - 5276

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Citation Number: 30

Abstract

However, the applicability of this method is limited to the availability of dialkylboranes. Direct hydroboration usually fails to stop at the dialkylborane state, generally proceeding to the trialkylborane stage. Only in the case of relatively hindered alkenes does direct hydroboration stop at the dialkylborane stage. Hence, Zweifel's synthesis of trans-alkenes and ketones has found limited application in organic synthesis. The second disadvantage ...