doi: 10.1021/ol062264h.
Highly concentrated catalytic asymmetric allylation of ketones
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- PMID: 17249767
- PMCID: PMC2526120
- DOI: 10.1021/ol062264h
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Highly concentrated catalytic asymmetric allylation of ketones
Org Lett.
.
Abstract
[reaction: see text] 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%).
Figures
Catalytic Asymmetric Allylation of Ketones in CH2Cl2 Solvent.
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