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Stereodivergent synthesis of alkenes by controllable syn-/anti-fragmentation of β-hydroxysulfonyl intermediates

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Abstract

The reduction of the carbonyl group in acylated trifluoroethyl alkanesulfonates follows the Felkin–Ahn selectivity, and the so-formed diastereomeric β-hydroxysulfonyl intermediates undergo syn- and anti-fragmentation, depending on the reaction conditions. In effect, isomeric E- and Z-alkenes are formed in a stereodivergent manner, which mimics the mechanistic manifold of the Peterson olefination.

Graphical abstract: Stereodivergent synthesis of alkenes by controllable syn-/anti-fragmentation of β-hydroxysulfonyl intermediates

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Publication details

The article was received on 13 Jul 2019, accepted on 22 Jul 2019 and first published on 22 Jul 2019


Article type: Communication
DOI: 10.1039/C9OB01563A
Org. Biomol. Chem., 2019, Advance Article

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    Stereodivergent synthesis of alkenes by controllable syn-/anti-fragmentation of β-hydroxysulfonyl intermediates

    B. Górski, D. Basiak, Ł. Grzesiński and M. Barbasiewicz, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB01563A

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