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Direct One-Pot Synthesis of α-Siloxy-Weinreb Amides from Aldehydes

Hisao Nemoto,* Rujian Ma, Hideki Moriguchi, Tomoyuki Kawamura, Masaki Kamiya and Masayuki Shibuya

*Department of Pharmaceutical Chemistry, Division of Health Biosciences, Graduate School of The University of Tokushima, 1-78-1, Tokushima, Japan 770-8505, Email: nemph.tokushima-u.ac.jp

H. Nemoto, R. Ma, H. Moriguchi, T. Kawamura, M. Kamiya, M. Shibuya, J. Org. Chem., 2007, 72, 9850-9853.

DOI: 10.1021/jo701859a (free Supporting Information)


Abstract

A one-pot method allows the synthesis of α-siloxy-Weinreb amides from aldehydes using N,O-dimethylhydroxylamine and a masked acyl cyanide reagent bearing a tert-butyldimethylsilyl group. The TBS group avoids the competitive reaction toward N-methoxy-N-methyl-2-amino-1-siloxymalononitrile.

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One-Pot Synthesis of α-Siloxy Esters Using a Silylated Masked Acyl Cyanide

H. Nemoto, R. Ma, T. Kawamura, K. Yatsuzuka, M. Kamiya, M. Shibuya, Synthesis, 2008, 3819-3827.


Key Words

α-hydroxy carbonyl compounds, α-hydroxy amides, Weinreb amides, multicomponent reactions


ID: J42-Y2007-4100