Gold-Catalyzed Iminations of Terminal Propargyl Alcohols with Anthranils with Atypical Chemoselectivity for C(1)-Additions and 1,2-Carbon Migration

Manisha Skaria, Sayaji Arjun More, Tung Chun Kuo, Mu Jeng Cheng, Rai Shung Liu

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

This work reports gold-catalyzed iminations of terminal propargyl alcohols with anthranils or isoxazoles to yield E-configured α-amino-2-en-1-ones and -1-als with complete chemoselectivity. These catalytic iminations occur exclusively with C(1)-nucleophilic additions on terminal alkynes, in contrast to a typical C(2)-route. For 3,3-dialkylprop-1-yn-3-ols, a methyl substituent is superior to long alkyl chains as the 1,2-migration groups toward α-imino gold carbenes. For secondary prop-1-yn-3-ols, phenyl, vinyl, and cyclopropyl substituents are better than hydrogen as the migrating groups, obviating typical gold carbene reactions. DFT calculations have been performed to rationalize the observed C(1)-regioselectivity and the preferable cyclopropyl migration based on gold carbene pathways.

Original languageEnglish
Pages (from-to)3600-3608
Number of pages9
JournalChemistry - A European Journal
Volume26
Issue number16
DOIs
Publication statusPublished - 2020 Mar 18

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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