Rh-Catalyzed Conjugate Addition of Arylzinc Chlorides to Thiochromones: A Highly Enantioselective Pathway for Accessing Chiral Thioflavanones

Ling Meng; Ming Yu Jin; Jun Wang

doi:10.1021/acs.orglett.6b02453

Rh-Catalyzed Conjugate Addition of Arylzinc Chlorides to Thiochromones: A Highly Enantioselective Pathway for Accessing Chiral Thioflavanones

Ling Meng, Ming Yu Jin, Jun Wang^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

41 Citations (Scopus)

Abstract

A highly efficient asymmetric synthesis of chiral thioflavanones is developed via conjugate addition of arylzinc reagents to thiochromones using Rh(COD)Cl2/(R)-3,4,5-MeO-MeOBIPHEP catalyst. This method overcomes catalyst poisoning and substrate inertness and affords a series of chiral thioflavanones (2-arylthiochroman-4-ones) in good yields (up to 91% yield) with excellent ee values (up to 97% ee). The established asymmetric synthesis paves the way for further pharmaceutical studies.

Original language	English
Pages (from-to)	4986–4989
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.6b02453
Publication status	Published - 7 Oct 2016

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title = "Rh-Catalyzed Conjugate Addition of Arylzinc Chlorides to Thiochromones: A Highly Enantioselective Pathway for Accessing Chiral Thioflavanones",

abstract = "A highly efficient asymmetric synthesis of chiral thioflavanones is developed via conjugate addition of arylzinc reagents to thiochromones using Rh(COD)Cl2/(R)-3,4,5-MeO-MeOBIPHEP catalyst. This method overcomes catalyst poisoning and substrate inertness and affords a series of chiral thioflavanones (2-arylthiochroman-4-ones) in good yields (up to 91% yield) with excellent ee values (up to 97% ee). The established asymmetric synthesis paves the way for further pharmaceutical studies.",

author = "Ling Meng and Jin, {Ming Yu} and Jun Wang",

note = "Funding information: We gratefully thank the startup fund from South University of Science and Technology of China and Shenzhen Basic Research Program (JCYJ20150630145302229) for financial support. Publisher copyright: {\textcopyright} 2016 American Chemical Society",

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doi = "10.1021/acs.orglett.6b02453",

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T1 - Rh-Catalyzed Conjugate Addition of Arylzinc Chlorides to Thiochromones

T2 - A Highly Enantioselective Pathway for Accessing Chiral Thioflavanones

AU - Meng, Ling

AU - Jin, Ming Yu

AU - Wang, Jun

N1 - Funding information: We gratefully thank the startup fund from South University of Science and Technology of China and Shenzhen Basic Research Program (JCYJ20150630145302229) for financial support. Publisher copyright: © 2016 American Chemical Society

PY - 2016/10/7

Y1 - 2016/10/7

N2 - A highly efficient asymmetric synthesis of chiral thioflavanones is developed via conjugate addition of arylzinc reagents to thiochromones using Rh(COD)Cl2/(R)-3,4,5-MeO-MeOBIPHEP catalyst. This method overcomes catalyst poisoning and substrate inertness and affords a series of chiral thioflavanones (2-arylthiochroman-4-ones) in good yields (up to 91% yield) with excellent ee values (up to 97% ee). The established asymmetric synthesis paves the way for further pharmaceutical studies.

AB - A highly efficient asymmetric synthesis of chiral thioflavanones is developed via conjugate addition of arylzinc reagents to thiochromones using Rh(COD)Cl2/(R)-3,4,5-MeO-MeOBIPHEP catalyst. This method overcomes catalyst poisoning and substrate inertness and affords a series of chiral thioflavanones (2-arylthiochroman-4-ones) in good yields (up to 91% yield) with excellent ee values (up to 97% ee). The established asymmetric synthesis paves the way for further pharmaceutical studies.

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U2 - 10.1021/acs.orglett.6b02453

DO - 10.1021/acs.orglett.6b02453

M3 - Journal article

SN - 1523-7060

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SP - 4986

EP - 4989

JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

Rh-Catalyzed Conjugate Addition of Arylzinc Chlorides to Thiochromones: A Highly Enantioselective Pathway for Accessing Chiral Thioflavanones

Abstract

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