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

Wang Linqing | Zendy; Yang Dongxu | Zendy; Li Dan | Zendy; Liu Xihong | Zendy; Wang Pengxin | Zendy; Wang Kezhou | Zendy; Zhu Haiyong | Zendy; Bai Lutao | Zendy; Wang Rui | Zendy

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

Author(s) -

Wang Linqing,

Yang Dongxu,

Li Dan,

Liu Xihong,

Wang Pengxin,

Wang Kezhou,

Zhu Haiyong,

Bai Lutao,

Wang Rui

Publication year - 2018

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201804177

Subject(s) - enantioselective synthesis , triphenylphosphine , triphenylphosphine oxide , phosphorus , catalysis , magnesium , chemistry , oxide , combinatorial chemistry , organic chemistry

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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