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Communication | Special issue | Vol 66, No. 1, 2005, pp.101-106
Published online, 14th October, 2005
DOI: 10.3987/COM-05-S(K)43
New Utilizations of Optically Active Homoallylamines: Highly Stereoselective Synthesis of Cyclic Guanidine and Thiourea

Reiko Yanada, Akira Kaieda, Kazuo Yanada, and Yoshiji Takemoto*

*Graduate School of Pharmaceutical Sciences, Kyoto University, 46-29 Yoshida-shimoadachi-machi, Sakyo-ku, Kyoto 606-8501, Japan


Halocyclizations of optically active homoallylguanidine and homoallylthiourea were examined. These reactions proceeded stereoselectively to give six membered cyclic guanidines and thiourea. High 1,3-asymmetric induction by the homoallylic substituents is observed in these halocyclizations.