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1. Radical zinc-atom-transfer-based carbozincation of haloalkynes with dialkylzincs

Author

Fabrice Chemla, Florian Dulong, Franck Ferreira, and Alejandro Pérez-Luna

Subjects
carbenoids, carbometallation, carbozincation, radicals, tandem reaction, Science, Organic chemistry, QD241-441
Abstract

The formation of alkylidenezinc carbenoids by 1,4-addition/carbozincation of dialkylzincs or alkyl iodides based on zinc atom radical transfer, in the presence of dimethylzinc with β-(propargyloxy)enoates having pendant iodo- and bromoalkynes, is disclosed. Formation of the carbenoid intermediate is fully stereoselective at −30 °C and arises from a formal anti-selective carbozincation reaction. Upon warming, the zinc carbenoid is stereochemically labile and isomerizes to its more stable form.

Published
2013
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