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Organocatalytic Sequential α-Amination/Corey-Chaykovsky Reaction of Aldehydes: A High Yield Synthesis of 4-Hydroxypyrazolidine Derivatives

B. Senthil Kumar, V. Venkataramasubramanian and Arumugam Sudalai*

*Chemical Engineering and Process Development Division, National Chemical Laboratory, Pashan Road, Pune-411 008, India, Email: a.sudalaincl.res.in

B. S. Kumar, V. Venkataramasubramanian, A. Sudalai, Org. Lett., 2012, 14, 2468-2471.

DOI: 10.1021/ol300739b (free Supporting Information)


Abstract

The in situ generation of α-amino aldehydes followed by reaction with dimethyloxosulfonium methylide under Corey-Chaykovsky reaction conditions gives 4-hydroxypyrazolidine derivatives in high yields with excellent enantio- and diastereoselectivities. This organocatalytic sequential method enables an efficient synthesis of anti-1,2-aminoalcohols.

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Key Words

Pyrazolidines, Corey-Chaykovsky Reaction, Organocatalysis


ID: J54-Y2012-1520