Highly enantioselective reaction of alpha-selenoorganolithium compounds with chiral bis(oxazoline)s and preparation of enantioenriched benzylidencyclohexanes

Shuichi Nakamura; Takayuki Aoki; Takahiro Ogura; Libo Wang; Takeshi Toru

doi:10.1021/jo048505l

Highly enantioselective reaction of alpha-selenoorganolithium compounds with chiral bis(oxazoline)s and preparation of enantioenriched benzylidencyclohexanes

J Org Chem. 2004 Dec 10;69(25):8916-23. doi: 10.1021/jo048505l.

Authors

Shuichi Nakamura¹, Takayuki Aoki, Takahiro Ogura, Libo Wang, Takeshi Toru

Affiliation

¹ Department of Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.

PMID: 15575774
DOI: 10.1021/jo048505l

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.