Journal
ORGANIC LETTERS
Volume 9, Issue 3, Pages 381-384Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol062264h
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Funding
- NIGMS NIH HHS [R01 GM058101-09, R01 GM058101-10, R01 GM058101, GM58101] Funding Source: Medline
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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%).
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