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Letter

Potassium Carbonate-Promoted Stereospecific 5-Endo-Trig Cyclization of Unactivated Allenes in the Absence of Any Transition Metals

Supporting Info

Hiroaki Ohno,*^† Yoichi Kadoh,^‡ Nobutaka Fujii,^† and Tetsuaki Tanaka*^‡;

Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan, and Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan

Org. Lett., 2006, 8 (5), pp 947–950

DOI: 10.1021/ol053094w

Publication Date (Web): February 7, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

†

Kyoto University.

‡

Osaka University.

, hohno@pharm.kyoto-u.ac.jp, ; , t-tanaka@phs.osaka-u.ac.jp

Abstract

Formation of 3-pyrrolines from simple unactivated allenes bearing a protected amino group under basic conditions is described. Treatment of α-amino allenes with potassium carbonate in DMF under reflux in the absence of any transition-metal catalysts gave the corresponding 3-pyrrolines in good to excellent yields, by 5-endo-trig mode cycloisomerization. The reaction of internal allenes with an axial chirality afforded the corresponding 3-pyrrolines in a stereoselective manner.

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Published In Issue March 02, 2006
Received December 21, 2005

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Letter

Potassium Carbonate-Promoted Stereospecific 5-Endo-Trig Cyclization of Unactivated Allenes in the Absence of Any Transition Metals