Catalytic enantioselective synthesis of chiral sulfonium ylides with S-stereogenic center

Wang，Xu Jie1; Liu，Huan Huan1; Cheng，Jun Kee1; Xiang，Shao Hua1,2; Tan，Bin1

2023

10.1016/j.chempr.2023.02.017

Chem   影响因子和分区

2451-9308

2451-9294

A sulfur stereogenic center is found in naturally occurring compounds and constitutes an important design element for pharmaceuticals and chiral auxiliaries. In view of the broad applications of S-stereogenic compounds, many methods were developed to enantioselectively construct the sulfur stereocenters. By contrast, the synthesis and isolation of S-stereogenic ylides was elusive although sulfonium ylides are important synthetic building blocks and such species have been proposed in the Doyle-Kirmse reaction. Using judicious substrate design, we have successfully developed the first catalytic enantioselective synthesis of sulfonium ylides with a chiral sulfur center. They are constructed from a broad array of sulfides in high yields (up to 98%) and enantioselectivities (up to 99%) through copper-catalyzed intramolecular carbene transfer reaction. The obtained ylides could be converted into alkylidenecyclopropanes with efficient sulfur-to-carbon chirality transfer.

alkylidenecyclopropanes chiral sulfonium ylide chirality transfer copper catalysis enantioselective synthesis Good Health and Well-being intramolecular carbene transfer sulfur stereogenic center

SCI

英语

第一 ; 通讯

Guangdong Provincial Key Laboratory Of Catalysis[2020B121201002];National Natural Science Foundation of China[21825105];National Natural Science Foundation of China[22231004];National Natural Science Foundation of China[22250410266];National Natural Science Foundation of China[22271135];

Chemistry

Chemistry, Multidisciplinary

WOS:001021143500001

CELL PRESS

2-s2.0-85159289668

Scopus

1.Shenzhen Grubbs Institute and,Department of Chemistry,Guangdong Provincial Key Laboratory of Catalysis,Southern University of Science and Technology,Shenzhen,518055,China
2.Academy for Advanced Interdisciplinary Studies,Southern University of Science and Technology,Shenzhen,518055,China

Wang，Xu Jie,Liu，Huan Huan,Cheng，Jun Kee,et al. Catalytic enantioselective synthesis of chiral sulfonium ylides with S-stereogenic center[J]. Chem,2023,9(6).

Wang，Xu Jie,Liu，Huan Huan,Cheng，Jun Kee,Xiang，Shao Hua,&Tan，Bin.(2023).Catalytic enantioselective synthesis of chiral sulfonium ylides with S-stereogenic center.Chem,9(6).

Wang，Xu Jie,et al."Catalytic enantioselective synthesis of chiral sulfonium ylides with S-stereogenic center".Chem 9.6(2023).