Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 42, Pages 18452-18456Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202007352
Keywords
asymmetric catalysis; boron; heterocycles; pyridine; reduction
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Funding
- National Natural Science Foundation of China [21871147, 91956106, 21602114]
- Fundamental Research Funds for Central Universities [2122018165]
- Tencent Foundation
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Herein, we report that highly chemoselective and enantioselective reduction of 2-vinyl-substituted pyridines has been achieved for the first time. The reaction, which uses chiral spiro-bicyclic bisboranes as catalysts and HBpin and an acidic amide as reducing reagents, proceeds through a cascade process involving 1,4-hydroboration followed by transfer hydrogenation of a dihydropyridine intermediate. The retained double bond in the reduction products permits their conversion to natural products and other useful heterocyclic compounds by simple transformations.
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