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- Title
Gold‐Catalyzed Iminations of Terminal Propargyl Alcohols with Anthranils with Atypical Chemoselectivity for C(1)‐Additions and 1,2‐Carbon Migration.
- Authors
Skaria, Manisha; More, Sayaji Arjun; Kuo, Tung‐Chun; Cheng, Mu‐Jeng; Liu, Rai‐Shung
- 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.
- Subjects
PROPARGYL alcohol; CHEMOSELECTIVITY; GOLD carbenes; ISOXAZOLES; YNOLS; ALKYNES
- Publication
Chemistry - A European Journal, 2020, Vol 26, Issue 16, p3600
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201905283