期刊
ACS CATALYSIS
卷 8, 期 2, 页码 1440-1447出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b04054
关键词
desymmetrization; asymmetric hydrogenation; rhodium; cyclohexadienones; cis-hydroindoles; cis-hydrobenzofurans
资金
- Department of Science and Technology (DST), New Delhi, India [SB/FT/CS-109/2013]
- DST
- UGC
Rhodium-catalyzed asymmetric hydrogenation of alkyne-tethered cyclohexadienones enables highly regio- and enantioselective reductive cyclization to afford cis-hydrobenzofurans and cis-hydroindoles in high yields. Desymmetrization of 1,3-diyne-tethered cyclohexadienones was also explored, wherein the intramolecular coordination of a Rh complex with the cyclohexadienone ring induces exclusive regioselectivity. Mechanistic studies including hydrogen deuterium crossover experiments suggested that hydrogen activation is the rate-determining step for tandem reductive cyclization. Moreover, this highly practical and atom-economical transformation has tolerance to many functional groups with a broad range of substrate scope, allowing further transformations to expand the structural complexity of the bicyclic scaffolds.
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