Journal of Organic Chemistry p. 715 - 721 (1983)
Update date:2022-09-26
Topics:
Goering, Harlan L.
Kantner, Steven S.
Tseng, Chung Chyi
Alkylation of allylic N-phenylcarbamates by deprotonation, complexation with CuI in THF, and addition of 1 equiv of RLi results in syn γ-alkylation in both cyclic and acyclic systems.This procedure gives higher stereo- and regiospecificity than when allylic N-phenylcarbamates are reacted with 3 equiv of etheral LiCuR2.A mechanism is presented which incorporates an intramolecular oxidative addition leading to a ?-allyl complex (3) which undergoes reductive elimination to give the syn γ-alkylation product.
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