title: Catalytic and highly enantioselective reactions of alpha-sulfonyl carbanions with chiral bis(oxazoline)s.
abstract: The enantioselective reactions of lithiated benzyl trifluoromethyl sulfones with a substoichiometric amount of a bis(oxazoline) and various aldehydes is disclosed. The products were formed with excellent diastereo- and enantioselectivities. Fluorination of the sulfone with N-fluorobenzenesulfonimide and a stoichiometric amount of a bis(oxazoline) gave products with extremely high enantioselectivities (up to 99% ee; ee=enantiomeric excess). The enantioselective reaction was confirmed to proceed through a dynamic thermodynamic resolution pathway.
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Nagoya 466-8555, Japan. snakamur@nitech.ac.jp
authors.forename: Shuichi
authors.initials: S
authors.lastname: Nakamura
authors.forename: Norimune
authors.initials: N
authors.lastname: Hirata
authors.forename: Ryusuke
authors.initials: R
authors.lastname: Yamada
authors.forename: Takeshi
authors.initials: T
authors.lastname: Kita
authors.forename: Norio
authors.initials: N
authors.lastname: Shibata
authors.forename: Takeshi
authors.initials: T
authors.lastname: Toru