ORGN 631 |
| Highly functionalized tetrahydro-1,2-oxazines with up to 3 stereogenic centers have been synthesized in excellent enantio- (≥99% e.e.) and complete diastereo-selectivities (>99:1 d.r.) in up to 90% yields, following a novel organocatalytic domino α-aminoxylation/aza-Michael reaction of acyclic nitroalkenals for asymmetric installation of both C-O and C-N bonds. Furthermore, DFT calculations reveal an unprecedented transition state in that a molecule of water assists the C-N bond forming step through dual H bonds.
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Heterocycles and Aromatics, Asymmetric Reactions and Syntheses and Total Synthesis of Complex Molecules
7:00 PM-9:00 PM, Wednesday, August 19, 2009 Walter E. Washington Convention Center -- Ballroom C, Poster
Division of Organic Chemistry |
