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Highly concentrated catalytic asymmetric allylation of ketones.

Organic letters (2007-01-26)
Alfred J Wooten, Jeung Gon Kim, Patrick J Walsh
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%).

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Titanium(IV) isopropoxide, 99.999% trace metals basis
Sigma-Aldrich
Titanium(IV) isopropoxide, 97%
Sigma-Aldrich
Titanium(IV) isopropoxide, ≥97.0%
Sigma-Aldrich
Titanium(IV) isopropoxide, packaged for use in deposition systems