title: Highly enantioselective reaction of alpha-selenoorganolithium compounds with chiral bis(oxazoline)s and preparation of enantioenriched benzylidencyclohexanes.
abstract: The enantioselective reaction of alpha-seleno carbanions derived from bis(phenylseleno)acetal and bis(2-pyridylseleno)acetal in the presence of bis(oxazoline)s with various electrophiles gave products with high enantioselectivity. The enantioselective reaction of alpha-lithio benzyl 2-pyridyl selenide gave the products with stereochemistry reverse to that obtained in the reaction of alpha-lithio benzyl phenyl selenide. Mechanistic investigation suggests the enantiodetermination of these reactions at -78 degrees C depends on dynamic thermodynamic resolution. The enantioselective reaction was applied to the preparation of enantioenriched olefins and epoxide.
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.
authors.forename: Shuichi
authors.initials: S
authors.lastname: Nakamura
authors.forename: Takayuki
authors.initials: T
authors.lastname: Aoki
authors.forename: Takahiro
authors.initials: T
authors.lastname: Ogura
authors.forename: Libo
authors.initials: L
authors.lastname: Wang
authors.forename: Takeshi
authors.initials: T
authors.lastname: Toru