Microwave-assisted aza-Prins reaction. Part 1: facile preparation of natural-like 3-azabicyclo[3.3.1]non-6-enes

TETRAHEDRON LETTERS

卷:52

Article

Parchinsky, Vladislav¹  Shumsky, Alexei¹  Krasavin, Mikhail^1,2 

[1] Chem Divers Res Inst, Chimki 141400, Moscow Reg, Russia

[2] Yaroslavl State Pedag Univ, Sci & Educ Ctr Innovat Res, Yaroslavl 150000, Russia

关键词: Microwave-assisted organic synthesis;    aza-Prins reaction;    Diastereoselective synthesis;    Bicyclic piperidines;    Lycopodium alkaloids;    Complexity-generating synthesis;   

DOI  :  10.1016/j.tetlet.2011.10.123

来源: Elsevier

【 摘 要 】

A facile and operationally simple route to diastereomerically pure, natural-like 3-azabicyclo[3.3.1]non-6-enes via microwave-assisted, BF3 center dot OEt2-promoted aza-Prins reaction has been developed. Complexity-generating transformations based on these products involving reactive functionalities introduced during the aza-Prins step have been developed. (C) 2011 Elsevier Ltd. All rights reserved.

【 授权许可】

Free