Acid-mediated coupling of γ-hydroxybutenolides and aldehydes: synthesis of a new class of spirocyclic ketal-lactones

TETRAHEDRON LETTERS

卷:53

Article

Munoz, Alberto¹  Murelli, Ryan P.^1,2 

[1] CUNY Brooklyn Coll, Dept Chem, Brooklyn, NY 11210 USA

[2] CUNY, Grad Ctr, Dept Chem, New York, NY 10016 USA

关键词: Spirocycles;    Prins reaction;    gamma-Hydroxybutenolides;   

DOI  :  10.1016/j.tetlet.2012.09.139

来源: Elsevier

【 摘 要 】

In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf), gamma-methyl-gamma-hydroxybutenolide reacts with aromatic aldehydes to generate a new class of stereochemically rich spirocyclic ketal-lactones in good yields and with excellent stereoselectivities. We believe that this process takes place through the in situ generation of protoanemonin followed by a Prins reaction. Herein, we describe this discovery, along with substrate scope and preliminary mechanistic studies. (C) 2012 Elsevier Ltd. All rights reserved.

【 授权许可】

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