84519-66-4Relevant articles and documents
Stereochemistry of the Wacker Reaction: Modes of Addition of Hydroxide, Methoxide, and Phenyl at High and Low [Cl-]. A Study Using Chirality Transfer
Hamed, Othman,Thompson, Charles,Henry, Patrick M.
, p. 7082 - 7083 (1997)
-
Alkylation of Allylic Derivates. 4. On the Mechanism of Alkylation of Allylic N-Phenylcarbamates with Lithium Dialkylcuprates
Goering, Harlan L.,Kantner, Steven S.,Tseng, Chung Chyi
, p. 715 - 721 (2007/10/02)
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.