Enantioselective reduction and sulfenylation of isoflavanone derivatives via bisguanidinium hypervalent silicate

Enantioselective reduction and sulfenylation of isoflavanone derivatives via bisguanidinium hypervalent silicate

In this work, we describe an enantioselective reduction and sulfenylation of isoflavanone derivatives by an ion pair strategy. The chiral cationic catalyst bisguanidinium (BG) is capable of chiral induction in catalytic systems. Silane hydride works as a reductant and helps to form an anionic hyperv...

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Bibliographic Details
Main Authors: Li, Qiaoqiang, Dai, Yuqing, Xu, Xinru, Wu, Wentao, Chen, Wenchao, Wang, Hong, Tan, Choon-Hong, Ye, Xinyi
Other Authors: School of Chemistry, Chemical Engineering and Biotechnology
Format: Article
Language:English
Published: 2024
Subjects:
Chemistry
Electrophilicity
Enantioselectivity
Online Access:https://hdl.handle.net/10356/180956
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Institution: Nanyang Technological University
Language: English
Description
Summary:In this work, we describe an enantioselective reduction and sulfenylation of isoflavanone derivatives by an ion pair strategy. The chiral cationic catalyst bisguanidinium (BG) is capable of chiral induction in catalytic systems. Silane hydride works as a reductant and helps to form an anionic hypervalent silicate complex and intermediates with substrates to pair with chiral catalyst. A series of umpolung sulfur reagents accomplish electrophilic attack in the presence of a silicate anion. Both chemoselectivity and enantioselectivity are good to excellent to afford a wide scope of 4-oxo-4H-chromene-3-carbonitrile and S-electrophilic reagents. Further transformations were completed to introduce more applications.

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