Catalytic asymmetric C-N bond formation: Phosphine-catalyzed intra- and intermolecular γ-addition of nitrogen nucleophiles to allenoates and alkynoates

Rylan J. Lundgren, Ashraf Wilsily, Nicolas Marion, Cong Ma, Ying Kit Chung, Gregory C. Fu

Research output: Journal article publicationJournal articleAcademic researchpeer-review

94 Citations (Scopus)

Abstract

Pin the amine on the gamma: A new method has been developed for the γ-addition of nitrogen nucleophiles to γ-substituted alkynoates or allenoates through intra- and intermolecular processes that are catalyzed by spirophosphine 1 (see scheme). An asymmetric version of this reaction affords enantioenriched pyrrolidines, indolines, and γ-amino-α,β- unsaturated carbonyl compounds.
Original languageEnglish
Pages (from-to)2525-2528
Number of pages4
JournalAngewandte Chemie - International Edition
Volume52
Issue number9
DOIs
Publication statusPublished - 25 Feb 2013
Externally publishedYes

Keywords

  • amination
  • asymmetric catalysis
  • heterocycles
  • organocatalysis
  • phosphanes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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