Journal of Organic Chemistry p. 863 - 871 (1995)
Update date:2022-08-11
Topics:
Meyer, Christophe
Marek, Ilane
Courtemanche, Gilles
Normant, Jean-F.
Polysubstituted enynes have been lithiated on the propargylic position, and transmetalation to the corresponding zinc reagents promotes an easy cyclization reaction leading to polysubstituted cyclopentylmethylzinc derivatives.This cyclization is stereospecific, and a single diastereoisomer is formed, even when a tertiary and a quaternary center are linked in the process.The reaction is considered to take place via a metallo-ene-allene process.
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