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Note | Special issue | Vol 67, No. 1, 2006, pp.433-436
Published online, 13th September, 2005
DOI: 10.3987/COM-05-S(T)59
A New and Convenient Access to Enantiopure C2-Symmetric 2,5-Diethynylpyrrolidine

Ikki Yonemura, Noriyuki Yasuda, Toshio Kawanami, Takeshi Hanamoto, Hiroshi Furuno, and Junji Inanaga*

*Institute for Fundamental Research of Organic Chemistry, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan

Abstract

Both (2R,5R)- and (2S,5S)-diethynylpyrrolidines were conveniently synthesized from 3,6-bis(mesyloxy)-1,7-octadiyne in optically pure forms via (R)-1-(4-methoxyphenyl)ethylamine-induced pyrrolidine ring formation, chromatographic separation of the corresponding diastereomers, and cleavage of the benzylic C-N bond.