The first catalytic, asymmetric α-additions of isocyanides. Lewis-base-catalyzed, enantioselective Passerini-type reactions

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Abstract

The first, catalytic, enantioselective α-additions of isocyanides to aldehydes have been demonstrated (Passerini-type reactions). The catalytic system of silicon tetrachloride and a chiral bisphosphoramide 5a provided high yields and good to excellent enantioselectivities for the addition of tert-butyl isocyanide to a wide range of aldehydes (aromatic, olefinic, acetylenic, aliphatic). Aqueous workup afforded the α-hydroxy tert-butyl amides, whereas methanolic quench followed by basic workup afforded the ∞-hydroxy methyl esters.

Original languageEnglish (US)
Pages (from-to)7825-7827
Number of pages3
JournalJournal of the American Chemical Society
Volume125
Issue number26
DOIs
StatePublished - Jul 2 2003

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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