ORGN 13 |
| A new stereoselective method for the synthesis of substituted tetrahydrofurans and pyrrolidines from gamma-hydroxy or gamma-amino alkenes and aryl or vinyl halides will be described. These reactions form both a carbon-carbon and a carbon-heteroatom bond in a single transformation, generating two or more stereocenters in one step with diastereoselectivities of up to >20:1. Preliminary mechanistic studies suggest the reactions proceed via the intramolecular insertion of an olefin into a Pd(Ar)(OR) or Pd(Ar)(NRR') intermediate. The structure of the Pd-catalyst has a dramatic influence on the relative rates of several competing mechanistic pathways, which allows for the selective synthesis of several different heterocyclic products from common starting materials by changing the nature of the catalyst. The scope and limitations of this methodology will be discussed, along with the use of these reactions in tandem processes and other applications. |
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Young Investigators Symposium
8:25 AM-12:00 PM, Sunday, 10 September 2006 Moscone Center -- Room 135, Oral
Division of Organic Chemistry |