ORGN 509 |
| Pd-catalyzed decarboxylative metalation is an efficient route for the coupling of two allyl species that avoids transmetalation. The decarboxylation of β-alkylidene malononitriles allows for the regiospecific generation of allyl anion equivalents and their reaction with electrophilic metal(allyl) complexes to assemble 1,5-dienes in high yield. Microwave assisted Cope rearrangement smoothly converts the kinetic hexadiene to a single thermodynamically stable α,β-unsaturated hexadiene product. In tandem, these two reactions provide hexadienes with high enantioselectivities and good diastereoselectivities when chiral palladium sources are employed.
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New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |
