Journal
ACS CATALYSIS
Volume 1, Issue 3, Pages 221-226Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cs100161k
Keywords
organocatalysis; cascade reaction; Michael addition; heterocycle; chromans
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Funding
- National Science Foundation of China [20872043, 2107269, 21002036]
- National Basic Research Program of China [2011CB808600]
- Program for Changjiang Scholars and Innovative Research Team in University [IRT0953]
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A highly enantioselective cascade reaction of benzotriazoles with nitroolefin-cotaining enonates catalyzed by a base/acid bifunctional organocatalyst has been developed. This cascade sequence affords efficient access to densely functionalized chiral chromans with a quaternary stereogenic center in high yield (up to 91%) with excellent enantioselectivity (up to 96% ee) and diastereoselectivity (up to 96:4 dr). The reaction itself features simple experimental procedures under benign conditions and is completely atom economic in character.
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