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)
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.
see article for more examples
H. Nemoto, R. Ma, T. Kawamura, K. Yatsuzuka, M. Kamiya, M. Shibuya, Synthesis, 2008, 3819-3827.