Highly Enantioselective Catalytic Cross-Dehydrogenative Coupling ofN-Carbamoyl Tetrahydroisoquinolines and Terminal Alkynes
Authors:
- 17 March 2015
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 17 (7) , 1684-1687
Abstract
The first catalytic asymmetric cross-dehydrogenative coupling of cyclic carbamates and terminal alkynes has been established. The reaction features high enantiocontrol and excellent functional group tolerance and displays a wide range of structurally and electronically diverse carbamates as well as terminal alkynes. N-Acyl hemiaminals were identified as the reactive intermediates through preliminary control experiments. Employing readily removable carbamates as substrates rather than traditionally adopted N-aryl amines allows applications in complex molecule synthesis and therefore advances the C–H functionalization strategy to a synthetically useful level.Keywords
Funding Information
- Program for New Century Excellent Talents in University (NCET-13-0346)
- National Natural Science Foundation of China (21202093, 21472112)
- Shandong Science Fund for Distinguished Young Scholars (JQ201404)
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