Pd/Zn Co-catalyzed Asymmetric Ring-Opening Reactions of Aza/Oxabicyclic Alkenes with Oximes

Guoli Shen; Ruhima Khan; Fan Yang; Yong Yang; Dongdong Pu; Yang Gao; Yong Zhan; Yang Luo; Baomin Fan

doi:10.1002/ajoc.201800569

Pd/Zn Co-catalyzed Asymmetric Ring-Opening Reactions of Aza/Oxabicyclic Alkenes with Oximes

Guoli Shen, Ruhima Khan, Fan Yang, Yong Yang^*, Dongdong Pu, Yang Gao, Yong Zhan, Yang Luo, Baomin Fan

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摘要

An application of various oximes as nucleophiles in the asymmetric ring-opening (ARO) reaction of aza/oxabicyclic alkenes resulting in cis-ARO products has been developed. The reaction was co-catalyzed by Pd(OAc)₂ and Zn(OTf)₂ with (R)-DIFLUORPHOS as the chiral ligand. This methodology exhibits broad substrate scope, functional group tolerance with high enantioselectivity. A synthetic application of this method has been demonstrated.

源语言	英语
页（从-至）	97-102
页数	6
期刊	Asian Journal of Organic Chemistry
卷	8
期	1
DOI	https://doi.org/10.1002/ajoc.201800569
出版状态	已出版 - 1月 2019
已对外发布	是

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Shen, G., Khan, R., Yang, F., Yang, Y., Pu, D., Gao, Y., Zhan, Y., Luo, Y., & Fan, B. (2019). Pd/Zn Co-catalyzed Asymmetric Ring-Opening Reactions of Aza/Oxabicyclic Alkenes with Oximes. Asian Journal of Organic Chemistry, 8(1), 97-102. https://doi.org/10.1002/ajoc.201800569

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title = "Pd/Zn Co-catalyzed Asymmetric Ring-Opening Reactions of Aza/Oxabicyclic Alkenes with Oximes",

abstract = "An application of various oximes as nucleophiles in the asymmetric ring-opening (ARO) reaction of aza/oxabicyclic alkenes resulting in cis-ARO products has been developed. The reaction was co-catalyzed by Pd(OAc)2 and Zn(OTf)2 with (R)-DIFLUORPHOS as the chiral ligand. This methodology exhibits broad substrate scope, functional group tolerance with high enantioselectivity. A synthetic application of this method has been demonstrated.",

keywords = "asymmetric catalysis, asymmetric synthesis, norbornadienes, oximes, ring-opening reactions",

author = "Guoli Shen and Ruhima Khan and Fan Yang and Yong Yang and Dongdong Pu and Yang Gao and Yong Zhan and Yang Luo and Baomin Fan",

note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2019",

month = jan,

doi = "10.1002/ajoc.201800569",

language = "English",

volume = "8",

pages = "97--102",

journal = "Asian Journal of Organic Chemistry",

issn = "2193-5807",

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T1 - Pd/Zn Co-catalyzed Asymmetric Ring-Opening Reactions of Aza/Oxabicyclic Alkenes with Oximes

AU - Shen, Guoli

AU - Khan, Ruhima

AU - Yang, Fan

AU - Yang, Yong

AU - Pu, Dongdong

AU - Gao, Yang

AU - Zhan, Yong

AU - Luo, Yang

AU - Fan, Baomin

PY - 2019/1

Y1 - 2019/1

N2 - An application of various oximes as nucleophiles in the asymmetric ring-opening (ARO) reaction of aza/oxabicyclic alkenes resulting in cis-ARO products has been developed. The reaction was co-catalyzed by Pd(OAc)2 and Zn(OTf)2 with (R)-DIFLUORPHOS as the chiral ligand. This methodology exhibits broad substrate scope, functional group tolerance with high enantioselectivity. A synthetic application of this method has been demonstrated.

AB - An application of various oximes as nucleophiles in the asymmetric ring-opening (ARO) reaction of aza/oxabicyclic alkenes resulting in cis-ARO products has been developed. The reaction was co-catalyzed by Pd(OAc)2 and Zn(OTf)2 with (R)-DIFLUORPHOS as the chiral ligand. This methodology exhibits broad substrate scope, functional group tolerance with high enantioselectivity. A synthetic application of this method has been demonstrated.

KW - asymmetric catalysis

KW - asymmetric synthesis

KW - norbornadienes

KW - oximes

KW - ring-opening reactions

UR - http://www.scopus.com/inward/record.url?scp=85055961998&partnerID=8YFLogxK

U2 - 10.1002/ajoc.201800569

DO - 10.1002/ajoc.201800569

M3 - Article

AN - SCOPUS:85055961998

SN - 2193-5807

VL - 8

SP - 97

EP - 102

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 1

ER -

Pd/Zn Co-catalyzed Asymmetric Ring-Opening Reactions of Aza/Oxabicyclic Alkenes with Oximes

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