Phosphine-catalyzed synthesis of β-lactones from ketenes and chiral β-oxyaldehydes

TETRAHEDRON LETTERS

卷:56

Article

Chen, Shi¹  Mondal, Mukulesh¹  Adams, Matthew P.¹  Wheeler, Kraig A.²  Kerrigan, Nessan J.¹ 

[1] Oakland Univ, Dept Chem, Rochester, MI 48309 USA

[2] Eastern Illinois Univ, Dept Chem, Charleston, IL 61920 USA

关键词: beta-Lactones;    Ketenes;    Phosphine;    Diastereoselective synthesis;    Chiral aldehydes;   

DOI  :  10.1016/j.tetlet.2015.09.141

来源: Elsevier

【 摘 要 】

In this Letter we describe a catalytic procedure for the diastereoselective synthesis of beta-lactones bearing up to three stereogenic centers, from disubstituted ketenes and chiral beta-oxyaldehydes. Tri-n-butylphosphine was determined to be the best catalyst with yields of up to 95% and moderate to good diastereos-electivity (dr up to 4:1) obtained in the formation of highly substituted beta-lactones. (C) 2015 Elsevier Ltd. All rights reserved.

【 授权许可】

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