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

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Draffin, W.N. and Harwood, L.M. orcid id iconORCID: https://orcid.org/0000-0002-8442-7380 (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 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.

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Item Type Article
URI https://reading-clone.eprints-hosting.org/id/eprint/11199
Identification Number/DOI 10.1055/s-2006-939054
Refereed Yes
Divisions Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
Uncontrolled Keywords ketone-derived azomethine ylide, 5,5-disubstituted prolines, Lewis, acid, stereoselective cycloaddition, AMINO-ACIDS, 5,5-DIMETHYLPROLINE, CONFORMATION
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