title: An organocascade kinetic resolution.
abstract: Products of a novel iminium-catalyzed oxa-Michael addition undergo a kinetic resolution by a subsequent enamine-catalyzed intermolecular reaction. This is a rare example of kinetic resolution by enamine catalysis and the first organocascade kinetic resolution. This resolution produces enantioenriched 2,6-cis-tetrahydropyrans and, notably, cascade products with absolute and relative configurations normally not observed using this diphenyl prolinol silyl ether. This resolution thus provides new insight into asymmetric induction in reactions employing this catalyst.
authors.affiliation: Department of Chemistry, Brooklyn College and the City University of New York, 2900 Bedford Avenue, Brooklyn, New York 11210, USA.
authors.forename: Patrick G
authors.initials: PG
authors.lastname: McGarraugh
authors.forename: Stacey E
authors.initials: SE
authors.lastname: Brenner-Moyer
mesh_terms: D002384:Catalysis; D007700:Kinetics; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D011759:Pyrrolidines / Q000737:chemistry; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D011714:Pyrans; D011759:Pyrrolidines; D012821:Silanes; C010509:prolinol
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