title: Nucleophilic displacement at benzhydryl centers: asymmetric synthesis of 1,1-diarylalkyl derivatives.
abstract: [reaction: see text] Activation of substituted 1,1-diarylmethanols as their corresponding toluenesulfonates and subsequent displacement with a range of carbon, nitrogen, oxygen, and sulfur nucleophiles proceeds in 81-96% yield. Enantiomerically enriched diarylmethanols 8a-c were activated and displaced with pyridine acetate enolate with complete stereochemical inversion at carbon to yield 1,1-diarylalkyl derivatives 10a-c without loss of optical purity.
authors.affiliation: Department of Process Research, Merck Frosst Centre for Therapeutic Research, P.O. Box 1005, Pointe Claire-Dorval, Québec, H9R 4P8, Canada.
authors.forename: Yuri
authors.initials: Y
authors.lastname: Bolshan
authors.forename: Cheng-yi
authors.initials: CY
authors.lastname: Chen
authors.forename: Jennifer R
authors.initials: JR
authors.lastname: Chilenski
authors.forename: Francis
authors.initials: F
authors.lastname: Gosselin
authors.forename: David J
authors.initials: DJ
authors.lastname: Mathre
authors.forename: Paul D
authors.initials: PD
authors.lastname: O'Shea
authors.forename: Amélie
authors.initials: A
authors.lastname: Roy
authors.forename: Richard D
authors.initials: RD
authors.lastname: Tillyer