79594-12-0Relevant academic research and scientific papers
Alkylation of Allylic Derivatives. 3. The Regiochemistry of Alkylation of the Isomeric trans-α,γ-Methylphenylallyl Acetates with Lithium Dialkyleuprates
Goering, Harlan N.,Seitz, Earl P.,Tseng, Chung Chyi
, p. 5304 - 5308 (1981)
Alkylation of the isomeric trans-α,γ-methylphenylallyl acetates (1-OAc and 2-OAc) with lithium dimethylcuprate or di-n-butylcuprate is regioselective but not regiospecific.Both isomers give essentially the same product mixture which contains 95percent of the trans conjugated alkylation product (3).The starting acetates do not rearrange under the conditions for these reactions.These results show that the isomeric acetate give the same product-forming intermediate(s).Presumably the key intermediate that is common to the two isomers is a ?-allyl copper(III).
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.
Regioselectivity in Organo-transition-metal Chemistry. A Remarkable Steric Effect in ?-Allyl Palladium Chemistry
Keinan, Ehud,Sahai, Mahendra
, p. 648 - 650 (2007/10/02)
The regioselectivity of the palladium catalysed allylic substitution by several representative nucleophiles was found to be highly dependent on very small steric differences that exist at the two ends of the allylic system: attack by stabilized nucleophil
