Asymmetric Ring-Opening Reactions of Aza- and Oxa-bicyclic Alkenes with Boronic Acids Using a Palladium/Zinc Co-catalytic System

Wei Zhang; Jingchao Chen; Guangzhi Zeng; Fan Yang; Jianbin Xu; Weiqing Sun; Madhuri Vikas Shinde; Baomin Fan

doi:10.1021/acs.joc.6b03038

Asymmetric Ring-Opening Reactions of Aza- and Oxa-bicyclic Alkenes with Boronic Acids Using a Palladium/Zinc Co-catalytic System

Wei Zhang, Jingchao Chen^*, Guangzhi Zeng, Fan Yang, Jianbin Xu, Weiqing Sun, Madhuri Vikas Shinde, Baomin Fan

^*Corresponding author for this work

Yunnan Minzu University

Research output: Contribution to journal › Article › peer-review

34 Citations (Scopus)

Abstract

The asymmetric ring opening reactions of bicyclic alkenes with boronic acids were accomplished by using a highly active palladium/zinc co-catalytic system that was suitable for both azabenzonorbornadienes and oxabenzonorbornadienes, which were transformed to the corresponding chiral hydronaphthalene products in high yields (up to 99%) and high optical purities (up to 98% ee). The reaction protocol is general and mild and displays good functional group tolerance.

Original language	English
Pages (from-to)	2641-2647
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	82
Issue number	5
DOIs	https://doi.org/10.1021/acs.joc.6b03038
Publication status	Published - 3 Mar 2017
Externally published	Yes

Access to Document

10.1021/acs.joc.6b03038

Cite this

@article{13a2fe8e9dc64609a018f625eb3d3333,

title = "Asymmetric Ring-Opening Reactions of Aza- and Oxa-bicyclic Alkenes with Boronic Acids Using a Palladium/Zinc Co-catalytic System",

abstract = "The asymmetric ring opening reactions of bicyclic alkenes with boronic acids were accomplished by using a highly active palladium/zinc co-catalytic system that was suitable for both azabenzonorbornadienes and oxabenzonorbornadienes, which were transformed to the corresponding chiral hydronaphthalene products in high yields (up to 99%) and high optical purities (up to 98% ee). The reaction protocol is general and mild and displays good functional group tolerance.",

author = "Wei Zhang and Jingchao Chen and Guangzhi Zeng and Fan Yang and Jianbin Xu and Weiqing Sun and Shinde, {Madhuri Vikas} and Baomin Fan",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

month = mar,

day = "3",

doi = "10.1021/acs.joc.6b03038",

language = "English",

volume = "82",

pages = "2641--2647",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "5",

}

TY - JOUR

T1 - Asymmetric Ring-Opening Reactions of Aza- and Oxa-bicyclic Alkenes with Boronic Acids Using a Palladium/Zinc Co-catalytic System

AU - Zhang, Wei

AU - Chen, Jingchao

AU - Zeng, Guangzhi

AU - Yang, Fan

AU - Xu, Jianbin

AU - Sun, Weiqing

AU - Shinde, Madhuri Vikas

AU - Fan, Baomin

PY - 2017/3/3

Y1 - 2017/3/3

N2 - The asymmetric ring opening reactions of bicyclic alkenes with boronic acids were accomplished by using a highly active palladium/zinc co-catalytic system that was suitable for both azabenzonorbornadienes and oxabenzonorbornadienes, which were transformed to the corresponding chiral hydronaphthalene products in high yields (up to 99%) and high optical purities (up to 98% ee). The reaction protocol is general and mild and displays good functional group tolerance.

AB - The asymmetric ring opening reactions of bicyclic alkenes with boronic acids were accomplished by using a highly active palladium/zinc co-catalytic system that was suitable for both azabenzonorbornadienes and oxabenzonorbornadienes, which were transformed to the corresponding chiral hydronaphthalene products in high yields (up to 99%) and high optical purities (up to 98% ee). The reaction protocol is general and mild and displays good functional group tolerance.

UR - http://www.scopus.com/inward/record.url?scp=85014525482&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.6b03038

DO - 10.1021/acs.joc.6b03038

M3 - Article

C2 - 28112930

AN - SCOPUS:85014525482

SN - 0022-3263

VL - 82

SP - 2641

EP - 2647

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 5

ER -

Asymmetric Ring-Opening Reactions of Aza- and Oxa-bicyclic Alkenes with Boronic Acids Using a Palladium/Zinc Co-catalytic System

Abstract

Access to Document

Other files and links

Fingerprint

Cite this