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Communication | Special issue | Vol 52, No. 2, 2000, pp.557-561
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S81
Synthesis of Homochiral β-Sulfinyl Nitrones and Their Application for Enantioselective Synthesis of (+)-Euphococcinine

Shun-Ichi Murahashi,* Jun Sun, Hiroyuki Kurosawa, and Yasushi Imada

*Department of Chemistry, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan


Homochiral β-sulfinyl nitrones can be prepared from secondary amines in three steps. Enantioselective synthesis of defensive alkaloid (+)-euphococcinine (9) has been accomplished by means of diastereoselective allylation of homochiral β-sulfinyl nitrone (13) followed by intramolecular 1,3-dipolar cycloaddition reaction.