The Important Role of the Byproduct Triphenylphosphine Oxide in the Magnesium(II)-Catalyzed Enantioselective Reaction of Hemiacetals and Phosphorus Ylides

Angewandte Chemie
Linqing WangRui Wang

Abstract

By employing a simple in situ generated magnesium catalyst, a direct asymmetric reaction between hemiacetals and phosphorus ylides was achieved through a tandem Wittig-oxa-Michael reaction sequence. Enantioenriched chromans, isochromans, and tetrahydropyrans were obtained in good chemical yields, and (-)-erythrococcamide B was synthesized in enantioenriched form. The byproduct triphenylphosphine oxide was identified as a necessary additive for this process.

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Citations

May 28, 2019·ChemistryOpen·Christopher SchwarzViktoria H Gessner
Oct 24, 2019·Angewandte Chemie·Alban FalconnetMagnus Rueping
Apr 18, 2020·Inorganic Chemistry·David Van CraenAmar H Flood

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