Iridium-Catalyzed Asymmetric Addition of Thiophenols to Oxabenzonorbornadienes

Sifeng Li; Zhiwu Lu; Ling Meng; Jun Wang

doi:10.1021/acs.orglett.6b02592

Iridium-Catalyzed Asymmetric Addition of Thiophenols to Oxabenzonorbornadienes

Sifeng Li
, Zhiwu Lu
, Ling Meng
, Jun Wang^*

^*Corresponding author for this work

Department of Chemistry

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

33 Citations (Scopus)

Abstract

A highly efficient asymmetric ring addition reaction of oxabenzonorbornadienes with thiophenols using an iridium/(S)-xyl-binap catalyst is developed. This catalyst system overcomes catalyst poisoning and background reactions and allows the formation of exclusive thiol addition products in high yields (up to 97% yield) with excellent enantioselectivities (up to 98% ee). Particularly noteworthy is that no competitive ring-opened side products are observed. X-ray crystal structure analysis confirmed the adduct is solely in the exo-configuration.

Original language	English
Pages (from-to)	5276–5279
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	20
DOIs	https://doi.org/10.1021/acs.orglett.6b02592
Publication status	Published - 21 Oct 2016

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title = "Iridium-Catalyzed Asymmetric Addition of Thiophenols to Oxabenzonorbornadienes",

abstract = "A highly efficient asymmetric ring addition reaction of oxabenzonorbornadienes with thiophenols using an iridium/(S)-xyl-binap catalyst is developed. This catalyst system overcomes catalyst poisoning and background reactions and allows the formation of exclusive thiol addition products in high yields (up to 97\% yield) with excellent enantioselectivities (up to 98\% ee). Particularly noteworthy is that no competitive ring-opened side products are observed. X-ray crystal structure analysis confirmed the adduct is solely in the exo-configuration.",

author = "Sifeng Li and Zhiwu Lu and Ling Meng and Jun Wang",

note = "Funding information: We gratefully thank National Natural Science Foundation of China (NSFC 21402081) for financial support. Prof. Zhongyuan Zhou of The Hong Kong Polytechnic University is gratefully acknowledged for X-ray crystallographic analysis of 3af. Publisher copyright: {\textcopyright} 2016 American Chemical Society",

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doi = "10.1021/acs.orglett.6b02592",

language = "English",

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T1 - Iridium-Catalyzed Asymmetric Addition of Thiophenols to Oxabenzonorbornadienes

AU - Li, Sifeng

AU - Lu, Zhiwu

AU - Meng, Ling

AU - Wang, Jun

N1 - Funding information: We gratefully thank National Natural Science Foundation of China (NSFC 21402081) for financial support. Prof. Zhongyuan Zhou of The Hong Kong Polytechnic University is gratefully acknowledged for X-ray crystallographic analysis of 3af. Publisher copyright: © 2016 American Chemical Society

PY - 2016/10/21

Y1 - 2016/10/21

N2 - A highly efficient asymmetric ring addition reaction of oxabenzonorbornadienes with thiophenols using an iridium/(S)-xyl-binap catalyst is developed. This catalyst system overcomes catalyst poisoning and background reactions and allows the formation of exclusive thiol addition products in high yields (up to 97% yield) with excellent enantioselectivities (up to 98% ee). Particularly noteworthy is that no competitive ring-opened side products are observed. X-ray crystal structure analysis confirmed the adduct is solely in the exo-configuration.

AB - A highly efficient asymmetric ring addition reaction of oxabenzonorbornadienes with thiophenols using an iridium/(S)-xyl-binap catalyst is developed. This catalyst system overcomes catalyst poisoning and background reactions and allows the formation of exclusive thiol addition products in high yields (up to 97% yield) with excellent enantioselectivities (up to 98% ee). Particularly noteworthy is that no competitive ring-opened side products are observed. X-ray crystal structure analysis confirmed the adduct is solely in the exo-configuration.

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DO - 10.1021/acs.orglett.6b02592

M3 - Journal article

SN - 1523-7060

VL - 18

SP - 5276

EP - 5279

JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

Iridium-Catalyzed Asymmetric Addition of Thiophenols to Oxabenzonorbornadienes

Abstract

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