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DOI: 10.1055/s-2008-1042719
Metal-Free Reduction of Tertiary Amides
Contributor(s):Benjamin List, Subhas Chandra PanUniversité de Montréal, Canada
Highly Chemoselective Metal-Free Reduction of Tertiary Amides
J. Am. Chem. Soc. 2008, 130: 18-19
Publication History
Publication Date:
21 February 2008 (online)
Key words
reduction - tertiary amides - Hantzsch esters - chemoselectivity
Significance
The authors report a chemoselective metal-free reduction of tertiary amides using Hantzsch ester 1 as the hydride source. Triflic anhydride was used as stoichiometric activating agent for this reaction. The authors have identified that functionalities such as esters, ketones, and epoxides are tolerated in their reaction and good to high yields (46-91%) are obtained for different tertiary amides.
Comment
Hantzsch esters have recently been used for different organocatalytic reductions (see reviews below). Here the authors have found that reduction of amides, which is typically a metal-mediated process, can be conducted in a metal-free fashion using Hantzsch esters. The high chemoselectivity of this process is quite attractive. A catalytic version would constitute a major advancement.
Reviews
S. J. Connon Org. Biomol. Chem. 2007, 5, 3407; S. L. You Chem. Asian J. 2007, 2, 820.