Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 16, Pages 3600-3608Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201905283
Keywords
1; 2-migration; alkynols; anthranils; C1-regioselectivity; gold catalysis; imination
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This work reports gold-catalyzed iminations of terminal propargyl alcohols with anthranils or isoxazoles to yield E-configured alpha-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 alpha-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.
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