Synthesis of enantio- and diastereoiso-merically pure substituted prolines via condensation of glycine with olefins activated by a carbonyl group
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 8,p. 2075-2083
- https://doi.org/10.1039/p19880002075
Abstract
The glycine fragment in the nickel(II) complex (1) formed from the Schiff′s base of glycine and (S)-o-[(N-benzylprolyl)amino]benzophenone (2) undergoes base-catalysed Michael addition to acrylaldehyde, α-methylacrylaldehyde, (E)-crotonaldehyde, (E)-cinnamaldehyde, and methyl vinyl ketone. No products of 1,2-addition were found in the Et3N-catalysed reactions. Addition followed by epimerization of the isomeric complexes proceeds with high diastereoselectivity at Cα(90%) and Cβ of the corresponding amino acid side chains. After chromatographic separation, the diastereoisomerically pure complexes were decomposed and the resulting dihydropyrrole-2-carboxylic acids reduced with NaBH3CN to give (S)-proline, trans-3-methyl-(S)-proline, trans-5-phenyl-(S)-proline, and a mixture of cis- and trans-5-methyl-(S)-prolines. The chiral auxiliary (2) was recovered in 80–90% yield.This publication has 8 references indexed in Scilit:
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