Scandium-Catalyzed Hydroxymethylation of Silicone Enolates
in Water

doi:10.1055/s-0028-1083426

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Synfacts 2008(11): 1174-1174
DOI: 10.1055/s-0028-1083426

Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions

Scandium-Catalyzed Hydroxymethylation of Silicone Enolates in Water

Contributor(s): Mark Lautens, Jane Panteleev
M. Kokubo, C. Ogawa, S. Kobayashi*
The University of Tokyo, Japan

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Publication History

Publication Date:
23 October 2008 (online)

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Significance

Lewis acid catalysis in aqueous media presents a formidable challenge because of catalyst instability and potential Lewis acid-Lewis base interactions with water. The authors report a scandium-catalyzed hydroxymethylation of silyl enolates with formaldehyde and water as the only solvent. A broad range of silenolethers react with high enantioselectivities. The method is applied to the synthesis of an artificial odorant.