Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 19, Pages 6039-6043Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b02607
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Funding
- JSPS KAKENHI [JP15H05755, JP15H05810]
- Program for Leading Graduate Schools: IGER Program in Green Natural Sciences (MEXT)
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Catalytic enantioselective halocyclization of 2-alkenylphenols and enamides have been achieved through the use of chiral amidophosphate catalysts and halo-Lewis acids. Density functional theory calculations suggested that the Lewis basicity of the catalyst played an important role in the reactivity and enantioselectivity. The resulting chiral halogenated chromans can be transformed to alpha-Tocopherol, alpha-Tocotrienol, Daedalin A and Englitazone in short steps. Furthermore, a halogenated product with an unsaturated side chain may provide polycyclic adducts under radical cyclization conditions.
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