Synlett 2006(20): 3419-3422  
DOI: 10.1055/s-2006-956466
LETTER
© Georg Thieme Verlag Stuttgart · New York

Aza-Mannich Condensation of Sulfinimine Promoted by Tetrabutyl­ammonium Fluoride: Synthesis of α,β-Unsaturated Sulfinimine

Xiaoxia Bian, Dan Zhang, Zhiyan Huang, Yong Qin*
Department of Chemistry of Medicinal Natural Products and Key Laboratory of Drug Targeting, West China School of Pharmacy and State Key Laboratory of Biotherapy, Sichuan University, Chengdu 610041, P. R. of China
e-Mail: yongqin@scu.edu.cn;
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Publication History

Received 12 July 2006
Publication Date:
08 December 2006 (online)

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Abstract

Self-condensation of tert-butanesulfinimine 5 was realized in the presence of tetrabutylammonium fluoride to afford α,β-unsaturated sulfinimine 8 in moderate to high yields with high geometric selectivities. The synthesized α,β-unsaturated sulfinimine 8 was demonstrated to be a versatile intermediate for the syntheses of enal 4 and chiral allyl amine 11.