α-Amino Aldehydes as Readily Available Chiral Aldehydes for Rh-Catalyzed Alkyne Hydroacylation

Joel F. Hooper, Sangwon Seo, Fiona R. Truscott, James D. Neuhaus, Michael C. Willis

Research output: Contribution to journalArticleResearchpeer-review

29 Citations (Scopus)

Abstract

Readily available α-amino aldehydes, incorporating a methylthiomethyl (MTM) protecting group on nitrogen, are shown to be efficient substrates in Rh-catalyzed alkyne hydroacylation reactions. The reactions are performed under mild conditions, employing a small-bite-angle bis-phosphine ligand, allowing for good functional group tolerance with high stereospecificity. Amino aldehydes derived from glycine, alanine, valine, leucine, phenylalanine, isoleucine, serine, tryptophan, methionine, and cysteine were successfully employed, as was an enantiomerically enriched α-OMTM-aldehyde derived from phenyllactic acid. The synthetic utility of the α-amino enone products is demonstrated in a short enantioselective synthesis of the natural product sphingosine.

Original languageEnglish
Pages (from-to)1630-1634
Number of pages5
JournalJournal of the American Chemical Society
Volume138
Issue number5
DOIs
Publication statusPublished - 17 Feb 2016
Externally publishedYes

Keywords

  • intramolecular hydroacylation
  • Rhodium
  • Aldehydes

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