Nucleophilic displacement at benzhydryl centers: Asymmetric synthesis of 1,1-diarylalkyl derivatives

被引：83

作者：

Bolshan, Y

Chen, CY

Chilenski, JR

Gosselin, F

Mathre, DJ

O'Shea, PD

Roy, A

Tillyer, RD

机构：

[1] Merck Frosst Ctr Therapeut Res, Dept Proc Res, Pointe Claire, PQ H9R 4P8, Canada

[2] Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 01期

关键词：

D O I：

10.1021/ol0361655

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：111 / 114

页数：4

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