Journal
ACS OMEGA
Volume 3, Issue 11, Pages 15492-15500Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsomega.8b01787
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Funding
- Texas Tech University
- National Science Foundation [CHE-1541685]
- NSF CRIF Program [CHE-1048553]
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Existing stereoselective routes to 2,5-cyclohexadienones involve either desymmetrization of an achiral substrate or have attempted to perform an asymmetric dearomatization of a phenol. Herein, we report proof-ofprinciple experiments aimed at developing a kinetic resolution as an alternative method for accessing enantioenriched 2,5-cyclohexadienones. More specifically, chiral bifunctional thiourea catalysts were used to promote the addition of 2-thionapthalene into unsymmetric para-quinols. The selectivity of the kinetic resolution was found to be quite sensitive to substitution around the substrate.
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