Highly concentrated catalytic asymmetric allylation of ketones

被引:52
|
作者
Wooten, Alfred J. [1 ]
Kim, Jeung Gon [1 ]
Walsh, Patrick J. [1 ]
机构
[1] Univ Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USA
关键词
D O I
10.1021/ol062264h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report the catalytic asymmetric allylation of ketones under highly concentrated reaction conditions with a catalyst generated from titanium tetraisopropoxide and BINOL (1:2 ratio) in the presence of isopropanol. This catalyst promotes the addition of tetraallylstannane to a variety of ketones to produce tertiary homoallylic alcohols in excellent yield (80-99%) with high enantioselectivities (79-95%). The resulting homoallylic alcohols can also be epoxidized in situ using tert-butyl hydroperoxide (TBHP) to afford cyclic epoxy alcohols in high yield (84-87%).
引用
收藏
页码:381 / 384
页数:4
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