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Synfacts 2007(9): 0941-0941  
DOI: 10.1055/s-2007-968866
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

syn-1,2-Amino Alcohols via Allylic C-H Amination

Contributor(s):Hisashi Yamamoto, Matthew B. Boxer
K. J. Fraunhoffer, M. C. White*
University of Illinois, Urbana, USA
syn-1,2-Amino Alcohols via Diastereoselective Allylic C-H Amination
J. Am. Chem. Soc.  2007,  129:  7274-7276  
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Publication History

Publication Date:
23 August 2007 (online)

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Key words

amino alcohols - C-H amination - palladium

Significance

Amino alcohols are unquestionably important compounds in biologically relevant settings. This paper describes a new approach for the diastereoselective synthesis of these compounds starting from a homoallylic alcohol derivative. Palladium catalyzed allylic C-H amination provides these important molecules in an expedient and selective manner.

Comment

The relatively high selectivity for this new process as well as the functionality of the product (alcohol, amine, and olefin) make this protocol extremely interesting. The White group has found quite a number of interesting uses for the Pd(II)-sulfoxide complex system. Allylic C-H functionalization seems to be a general trend, making this catalyst class quite intriguing for future exploitation.

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