An expeditious synthesis of 4-fluoropiperidines via aza-Prins cyclization

作者：Yadav J S^*; Reddy B V Subba; Ramesh K; Kumar G G K S Narayana; Gree Rene

来源：Tetrahedron Letters, 2010, 51(12): 1578-1581.

DOI：10.1016/j.tetlet.2010.01.059

• Aza-Prins cyclization
• Tetrafluoroboric acid
• Homoallylic amines
• 4-Fluoropiperidines

The reaction of aldehydes with N-tosyl homoallylamine in the presence Of a Solution of tetrafluoroboric acid-diethyl ether complex in dichloromethane at ambient temperature gave the 4-fluoropiperidines in good yields and with high cis-selectivity. This aza-Prins-type cyclization has a wide scope and the use of HBF(4) OEt(2) makes this procedure simple, convenient, and cost-effective for the preparation of 4-fluoropiperidines.

• 出版日期2010-3-24