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

^*Corresponding author for this work

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

12 Citations (Scopus)

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.

Original language	English
Pages (from-to)	97-102
Number of pages	6
Journal	Asian Journal of Organic Chemistry
Volume	8
Issue number	1
DOIs	https://doi.org/10.1002/ajoc.201800569
Publication status	Published - Jan 2019
Externally published	Yes

Keywords

asymmetric catalysis
asymmetric synthesis
norbornadienes
oximes
ring-opening reactions

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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",

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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 - https://www.scopus.com/pages/publications/85055961998

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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Keywords

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