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

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.

Key words

metalate rearrangement - lithium - copper - tin - trisubstituted olefins

References

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