Issue 8, 1988
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Synthesis of enantio- and diastereoiso-merically pure substituted prolines via condensation of glycine with olefins activated by a carbonyl group

Yuri N. Belokoń,   Aleksandr G. Bulychev,   Viacheslav A. Pavlov,   Eugenia B. Fedorova,   Vladimir A. Tsyryapkin,   Vladimir A. Bakhmutov  and  Vasili M. Belikov  

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.

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Article information

DOI
https://doi.org/10.1039/P19880002075
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1988, 2075-2083

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Synthesis of enantio- and diastereoiso-merically pure substituted prolines via condensation of glycine with olefins activated by a carbonyl group

Y. N. Belokoń, A. G. Bulychev, V. A. Pavlov, E. B. Fedorova, V. A. Tsyryapkin, V. A. Bakhmutov and V. M. Belikov, J. Chem. Soc., Perkin Trans. 1, 1988, 2075 DOI: 10.1039/P19880002075

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