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

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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 nem@ph.tokushima-u.ac.jp

J. Org. Chem., 2007, 72 (25), pp 9850–9853

DOI: 10.1021/jo701859a

Publication Date (Web): November 8, 2007

Section:

Organometallic and Organometalloidal Compounds

Abstract

A one-pot method for synthesizing α-siloxy-Weinreb amides from aldehydes was developed with use of N,O-dimethylhydroxylamine and a masked acyl cyanide reagent bearing a tert-butyldimethylsilyl group avoiding the competitive reaction toward N-methoxy-N-methyl-2-amino-1-siloxymalononitrile.

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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

A Powerful Reagent for Synthesis of Weinreb Amides Directly from Carboxylic Acids
Teng Niu, Weiming Zhang, Danfeng Huang, Changming Xu, Haifeng Wang and Yulai Hu
Organic Letters2009 11 (19), 4474-4477
- A Powerful Reagent for Synthesis of Weinreb Amides Directly from Carboxylic Acids
  Teng Niu, Weiming Zhang, Danfeng Huang, Changming Xu, Haifeng Wang and Yulai Hu
  Organic Letters2009 11 (19), 4474-4477
  A powerful reagent, P[NCH3(OCH3)]3 (3), for conversion of carboxylic acids directly to Weinreb amides was developed. In most cases the yields of the corresponding Weinreb amides were above 90% when P[NCH3(OCH3)]3 was heated with aromatic and aliphatic ...
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Synthesis of Weinreb Amides via Pd-Catalyzed Aminocarbonylation of Heterocyclic-Derived Triflates
A. Deagostino, Paolo Larini, Ernesto G. Occhiato, Lorena Pizzuto, Cristina Prandi, and Paolo Venturello
The Journal of Organic Chemistry2008 73 (5), 1941-1945
- Synthesis of Weinreb Amides via Pd-Catalyzed Aminocarbonylation of Heterocyclic-Derived Triflates
  A. Deagostino, Paolo Larini, Ernesto G. Occhiato, Lorena Pizzuto, Cristina Prandi, and Paolo Venturello
  The Journal of Organic Chemistry2008 73 (5), 1941-1945
  The direct transformation of lactam-, lactone-, and thiolactone-derived triflates into N-methoxy-N-methyl or morpholine Weinreb amides has been realized using Pd-catalyzed aminocarbonylation under CO atmospheric pressure and at room temperature. The ...
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