Stereodivergent synthesis of alkenes by controllable syn-/anti-fragmentation of β-hydroxysulfonyl intermediates?
Organic & Biomolecular Chemistry Pub Date: 2019-07-22 DOI: 10.1039/C9OB01563A
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.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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