Access to chiral HWE reagents by rhodium-catalyzed asymmetric arylation of γ,δ-unsaturated β-ketophosphonates

Access to chiral HWE reagents by rhodium-catalyzed asymmetric arylation of γ,δ-unsaturated β-ketophosphonates

Asymmetric arylation of γ,δ-unsaturated β-ketophosphonates with arylboronic acids is reported. By using the (R)-diene* ligated rhodium(I) chloride complex as a catalyst under none basic conditions, the corresponding β-ketophosphonates bearing a δ-chiral center were obtained in high yields (up to 99%...

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Bibliographic Details
Main Authors: Yin, Long, Zhang, Dewei, Xing, Junhao, Wang, Yuhan, Wu, Changhui, Lu, Tao, Chen, Yadong, Hayashi, Tamio, Dou, Xiaowei
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2020
Subjects:
Science::Chemistry
Stereoselectivity
Catalysts
Online Access:https://hdl.handle.net/10356/139657
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Institution: Nanyang Technological University
Language: English
Description
Summary:Asymmetric arylation of γ,δ-unsaturated β-ketophosphonates with arylboronic acids is reported. By using the (R)-diene* ligated rhodium(I) chloride complex as a catalyst under none basic conditions, the corresponding β-ketophosphonates bearing a δ-chiral center were obtained in high yields (up to 99%) with good to excellent enantioselectivities (up to >99% ee). The enantioenriched products can be readily converted to diverse chiral β′-aryl enones by the Horner–Wadsworth–Emmons reaction.

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