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1.
J Org Chem ; 78(16): 8074-82, 2013 Aug 16.
Article in English | MEDLINE | ID: mdl-23862687

ABSTRACT

The first reported examples of kinetic resolution in epoxidation reactions using iminium salt catalysis are described, providing up to 99% ee in the epoxidation of racemic cis-chromenes.


Subject(s)
Epoxy Compounds/chemical synthesis , Imines/chemistry , Catalysis , Epoxy Compounds/chemistry , Kinetics , Molecular Conformation , Salts/chemistry , Stereoisomerism
2.
Org Lett ; 11(9): 1991-3, 2009 May 07.
Article in English | MEDLINE | ID: mdl-19354231

ABSTRACT

Concise highly enantioselective three-step syntheses are described for (-)-(3'S)-lomatin and (+)-(3'S,4'R)-trans-khellactone from 7-hydroxycoumarin in 97% ee and in 57% and 58% overall yields, respectively, using nonaqueous enantioselective epoxidation by an iminium salt as the key step.


Subject(s)
Coumarins/chemistry , Coumarins/chemical synthesis , Crystallography, X-Ray , Molecular Structure , Stereoisomerism , Umbelliferones/chemistry
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