Journal
ACS CATALYSIS
Volume 10, Issue 1, Pages 51-55Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b03874
Keywords
heteroarene dearomatization; asymmetric catalysis; heterocycles; rhodium catalysis; dihydropyridines
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Funding
- Auburn University
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Enantioselective synthesis of nonaromatic heterocycles containing a fully substituted stereogenic center is a challenging synthetic problem. We describe a strategy toward this problem involving dearomatization of N-alkylpyridinium salts using boronic acid nucleophiles. This dearomatization reaction is catalyzed by a rhodium(I)/BINAP catalytic system and delivers dihydropyridines that contain a fully substituted stereogenic center alpha to the ring nitrogen atom in high yields and enantioselectivities. The reaction is compatible with a wide range of functional groups such as halide, ester, amide, olefin, and free alcohol. Derivatization of dehydropyridine products allows synthesis of the functionalized tetrahydropyridines and piperidines.
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