ORGN 680 |
| Succinic anhydrides containing both a tethered terminal olefin and a 1,2-disubstituted olefin were prepared by subjecting cis-norbornene-endo-2,3-dicarboxylic anhydride to ring opening metathesis/cross metathesis (ROM/CM) conditions with various terminal olefins. The tethered terminal olefin, rather than the 1,2-disubstituted olefin, directs a nickel-catalyzed alkylation of these substituted succinic anhydrides with diorganozinc reagents. The reaction affords 1,4-ketoacids in high yields and high regioselectivities. The opposite regioisomers are obtained when the terminal olefins of these succinic anhydrides are reduced. Reduction of both olefins results in an unselective alkylation of these succinic anhydrides.
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New Reactions and Methodology
1:00 PM-5:00 PM, Wednesday, 13 September 2006 Moscone Center -- Room 133, Oral
Division of Organic Chemistry |
