ORGN 458 |
Asymmetric catalysis utilising imidazoles
| Helen C. Norton and Simon Jones. Department of Chemistry, University of Sheffield, Sheffield, S3 7HF, United Kingdom |
Nucleophilic catalyst 1 has been proposed for the resolution of secondary alcohols by acyl or phosphoryl group transfer. The N-methylimidazole (NMI) moiety is employed as the nucleophilic component and chirality is transferred to the product using a chiral oxazoline group. Such compounds also have potential as bidentate ligands for a wide range of asymmetric transformations. The most successful synthesis of target 1 relies on the addition of the amino alcohol to N-methyl imidazole methyl ester. Phosphate formation followed by cyclisation gave catalyst 1 in good yield. Preliminary evaluation of catalyst 1 as an acyl transfer catalyst was carried out using conditions described by Fu. With the aid of molecular modelling, analogues 2 and 3 have also been prepared and evaluated.  |
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Total Synthesis, Asymmetric Reactions and Syntheses, Bioorganic
9:00 AM-11:00 AM, Wednesday, March 31, 2004 Anaheim Convention Center -- Hall C, Poster
Division of Organic Chemistry
The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004
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