ORGN 557 |
| The novel osmium-catalysed oxidative cyclisation of N-protected amino alcohols to form 2,5-syn-pyrrolidines or 2,5-syn THFs has been developed. The transformation has been shown to proceed in good to excellent yields and to tolerate catalyst loadings as low as 0.2 mol% after optimisation of reaction conditions. The reaction is stereoselective with respect to formation of 2,5-syn products and stereospecific with respect to addition across the alkene moiety, as confirmed by X-ray crystallography. Furthermore, use of enantiopure starting materials allows synthesis of enantiopure heterocycle products.
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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 |
