84519-65-3Relevant academic research and scientific papers
Copper-catalyzed γ-selective and stereospecific allyl-aryl coupling between (Z)-acyclic and cyclic allylic phosphates and arylboronates
Ohmiya, Hirohisa,Yokokawa, Natsumi,Sawamura, Masaya
supporting information; experimental part, p. 2438 - 2440 (2010/07/10)
A Cu-catalyzed allyl-aryl coupling reaction between (Z)-acyclic or cyclic allylic phosphates and arylboronates proceeds with excellent γ-E-selectivity and 1,3-anti chirality transfer, which gives the corresponding coupling products with benzylic and allylic stereogenic centers. The wide availability and easy-to-handle nature of arylboronates, the inexpensiveness of the Cu catalyst system, and the high regio- and stereoselectivities are attractive features of this protocol.
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.
