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. 2006 Sep 28;8(20):4413-6.
doi: 10.1021/ol061417y.

Catalytic asymmetric methallylation of ketones with an (H8-BINOLate)Ti-based catalyst

Jeung Gon Kim  1 , Elizabeth H Camp, Patrick J Walsh
Affiliations

Catalytic asymmetric methallylation of ketones with an (H8-BINOLate)Ti-based catalyst

Jeung Gon Kim et al. Org Lett. .

Abstract

The first catalytic asymmetric methallylation of ketones is reported. The catalyst, which is generated from titanium tetraisopropoxide, H8-BINOL, 2-propanol, and tetramethallylstannane, reacts with ketones in acetonitrile to afford tertiary homoallylic alcohols in fair to excellent yields (55-99%) and fair to high enantioselectivities (46-90%). Ozonolysis of the resulting products provides access to chiral beta-hydroxy ketones, which are not readily prepared from direct asymmetric aldol reaction of acetone with ketones.

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Figures

Scheme 1
Scheme 1
Scheme 2
Scheme 2
Catalytic Asymmetric Allylation of Ketones
Figure 1
Figure 1
Additional Axially Chiral Ligands Tested
Scheme 3
Scheme 3
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