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Synthesis of enantiopure prolines via exo-stereoselective 1,3-dipolar cycloadditions to acetone-derived chiral stabilised azomethine ylides

Draffin, W.N. and Harwood, L.M. (2006) Synthesis of enantiopure prolines via exo-stereoselective 1,3-dipolar cycloadditions to acetone-derived chiral stabilised azomethine ylides. Synlett, 2006 (6). pp. 857-860. ISSN 0936-5214

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To link to this article DOI: 10.1055/s-2006-939054

Abstract/Summary

The chiral stabilised azomethine ylide formed from condensation of the dimethyl acetal of acetone with (5S)-5-phenylmorpholinone undergoes stereoselective exo-cycloaddition reactions with a range of doubly and singly activated dipolarophiles when generated in the presence of excess (MgBr2OEt2)-O-.. The cycloadducts can be degraded to yield enantiomerically pure proline derivatives.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:11199
Uncontrolled Keywords:ketone-derived azomethine ylide, 5,5-disubstituted prolines, Lewis, acid, stereoselective cycloaddition, AMINO-ACIDS, 5,5-DIMETHYLPROLINE, CONFORMATION

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