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Stereoselective deconjugation of macrocyclic α,β-unsaturated esters by sequential amidation and olefin transposition: application to enantioselective phase transfer catalysis

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Published in Organic and Biomolecular Chemistry. 2019, vol. 17, no. 28, p. 6905-6910
Abstract The stereoselective synthesis of chiral macrocycles bearing two aliphatic amide functional groups is reported. After the amidation mediated by TBD, a guanidine derivative, the olefin transposition step is performed with a slight excess of t-BuOK. The products are afforded in moderate to good combined yields (up to 59%) and with an excellent syn diastereoselectivity (dr > 49 : 1). Introducing enantiopure α-branched substituents was possible and it resulted in mixtures of diastereomers, which could be tested as phase-transfer catalysts using the formation of a phenylalanine analog as a test reaction (up to 43% ee). A clear matched–mismatched situation was observed in the two diastereomeric series.
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Research group Groupe Lacour
Projects FNS: 200020-172497
FNS: 200020-184843
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HOMBERG, Alexandre et al. Stereoselective deconjugation of macrocyclic α,β-unsaturated esters by sequential amidation and olefin transposition: application to enantioselective phase transfer catalysis. In: Organic and Biomolecular Chemistry, 2019, vol. 17, n° 28, p. 6905-6910. https://archive-ouverte.unige.ch/unige:120385

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Deposited on : 2019-07-05

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