Premium
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.