Cu(I)-Catalyzed Enantioselective Alkynylation of Thiochromones

Ling Meng; Ka Yan Ngai; Xiaoyong Chang; Zhenyang Lin; Jun Wang

doi:10.1021/acs.orglett.0c00005

Cu(I)-Catalyzed Enantioselective Alkynylation of Thiochromones

Ling Meng, Ka Yan Ngai, Xiaoyong Chang, Zhenyang Lin^*, Jun Wang^*

^*Corresponding author for this work

Department of Chemistry

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

17 Citations (Scopus)

Abstract

A highly efficient asymmetric synthesis of chiral thiochromanones is developed via Cu(I)/phosphoramidite catalyzed asymmetric alkynylation of thiochromones under mild reaction conditions. The catalyst system is tolerant of various thiochromone precursors and terminal alkynes. The established asymmetric transformation provides different enatiomeric-enriched thiochromanones with more molecular complexity and enables access to chiral thioflavanones, a subgroup of flavonoid by further functionalization.

Original language	English
Pages (from-to)	1155–1159
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	3
DOIs	https://doi.org/10.1021/acs.orglett.0c00005
Publication status	Published - 7 Feb 2020

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10.1021/acs.orglett.0c00005

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title = "Cu(I)-Catalyzed Enantioselective Alkynylation of Thiochromones",

abstract = "A highly efficient asymmetric synthesis of chiral thiochromanones is developed via Cu(I)/phosphoramidite catalyzed asymmetric alkynylation of thiochromones under mild reaction conditions. The catalyst system is tolerant of various thiochromone precursors and terminal alkynes. The established asymmetric transformation provides different enatiomeric-enriched thiochromanones with more molecular complexity and enables access to chiral thioflavanones, a subgroup of flavonoid by further functionalization.",

author = "Ling Meng and Ngai, {Ka Yan} and Xiaoyong Chang and Zhenyang Lin and Jun Wang",

note = "Funding information: We gratefully acknowledge Shenzhen Overseas High-level Talents Innovation Plan of Technical Innovation Project (KQJSCX20180319114439973) and the Research Grants Council of Hong Kong (HKUST 16304416) for financial support. Publisher copyright: {\textcopyright} 2020 American Chemical Society",

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doi = "10.1021/acs.orglett.0c00005",

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TY - JOUR

T1 - Cu(I)-Catalyzed Enantioselective Alkynylation of Thiochromones

AU - Meng, Ling

AU - Ngai, Ka Yan

AU - Chang, Xiaoyong

AU - Lin, Zhenyang

AU - Wang, Jun

N1 - Funding information: We gratefully acknowledge Shenzhen Overseas High-level Talents Innovation Plan of Technical Innovation Project (KQJSCX20180319114439973) and the Research Grants Council of Hong Kong (HKUST 16304416) for financial support. Publisher copyright: © 2020 American Chemical Society

PY - 2020/2/7

Y1 - 2020/2/7

N2 - A highly efficient asymmetric synthesis of chiral thiochromanones is developed via Cu(I)/phosphoramidite catalyzed asymmetric alkynylation of thiochromones under mild reaction conditions. The catalyst system is tolerant of various thiochromone precursors and terminal alkynes. The established asymmetric transformation provides different enatiomeric-enriched thiochromanones with more molecular complexity and enables access to chiral thioflavanones, a subgroup of flavonoid by further functionalization.

AB - A highly efficient asymmetric synthesis of chiral thiochromanones is developed via Cu(I)/phosphoramidite catalyzed asymmetric alkynylation of thiochromones under mild reaction conditions. The catalyst system is tolerant of various thiochromone precursors and terminal alkynes. The established asymmetric transformation provides different enatiomeric-enriched thiochromanones with more molecular complexity and enables access to chiral thioflavanones, a subgroup of flavonoid by further functionalization.

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U2 - 10.1021/acs.orglett.0c00005

DO - 10.1021/acs.orglett.0c00005

M3 - Journal article

SN - 1523-7060

VL - 22

SP - 1155

EP - 1159

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

Cu(I)-Catalyzed Enantioselective Alkynylation of Thiochromones

Abstract

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