Nucleophilic displacement at benzhydryl centers: asymmetric synthesis of 1,1-diarylalkyl derivatives.
[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.
Bolshan
Yuri
Y
Department of Process Research, Merck Frosst Centre for Therapeutic Research, P.O. Box 1005, Pointe Claire-Dorval, Québec, H9R 4P8, Canada.
Chen
Cheng-yi
CY
Chilenski
Jennifer R
JR
Gosselin
Francis
F
Mathre
David J
DJ
O'Shea
Paul D
PD
Roy
Amélie
A
Tillyer
Richard D
RD