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.
|Original language||English (US)|
|Number of pages||4|
|State||Published - Dec 16 2011|
All Science Journal Classification (ASJC) codes
- Physical and Theoretical Chemistry
- Organic Chemistry