Synthesis of Geminal Dimetal-Substituted Terminal Alkenes Utilizing a Cuprate Rearrangement: Toward an Efficient and General Access to Trisubstituted Olefins

P Le Menez, JD Brion, N Lensen, E Chelain…

Index: Menez, Patrick Le; Brion, Jean-Daniel; Lensen, Nathalie; Chelain, Evelyne; Pancrazi, Ange; Ardisson, Janick Synthesis, 2003 , # 16 p. 2530 - 2534

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Citation Number: 7

Abstract

Abstract Preparation of 1, 1-dimetalated-1-alkenes was realised via metalate rearrangements in the opening of lithiodihydrofuran 6 by reaction with dilithium stannyl-, silyl- , alkyl-and aryl (cyano) cuprates and quenching with electrophilic agents. Several hetero (E)- and (Z)-1, 1-dimetalated alkene derivatives were so produced in good to high yields and total stereocontrol.