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.
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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Pyrazolidines, Corey-Chaykovsky Reaction, Organocatalysis