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Synfacts 2010(7): 0799-0799  
DOI: 10.1055/s-0029-1220111
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereoselective Aldol Reaction of ;N-Trimethylsilyloxyenamines

Contributor(s): Hisashi Yamamoto, Zhi Li
M. R. Sonawane, I. CÍsaŘovÁ, I. M. Lyapkalo*
Charles University, Prague, Czech Republic
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Publication History

Publication Date:
22 June 2010 (online)

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Significance

In this report, a new aldehyde enolate equivalent, N-trimethylsilyloxyenamine, has been developed for aldol reactions. The enamines were obtained from condensation of the corresponding aldehyde and tert-butylhydroxylamine followed by TMS protection. The aldol products are corresponding nitrones, which could be hydrolyzed with reasonable selectivity erosions.