Silylated Pyrrolidines as Catalysts for Asymmetric Michael Additions of Aldehydes to Nitroolefins

Abstract

Silicon can! A convenient synthesis of enantiopure (S)-2-(diphenylmethylsilyl)pyrrolidine is described and its organocatalytic activity in asymmetric Michael reactions is demonstrated (see scheme). By using 10 mol % of this novel organocatalyst, the addition of aldehydes to nitroolefins affords products with high stereoselectivities (d.r. ≤97:3 and e.r. ≤95:5) in yields up to 99 %. Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.