Rhodium/zinc co-catalyzed asymmetric ring opening reactions of oxabenzonorbornadienes with carboxylic acids

Xiaobo He; Jingchao Chen; Xin Xu; Fan Yang; Cuiping Gu; Yongyun Zhou; Baomin Fan

doi:10.1016/j.tetasy.2016.11.004

Rhodium/zinc co-catalyzed asymmetric ring opening reactions of oxabenzonorbornadienes with carboxylic acids

Xiaobo He, Jingchao Chen^*, Xin Xu, Fan Yang, Cuiping Gu, Yongyun Zhou, Baomin Fan

^*Corresponding author for this work

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

13 Citations (Scopus)

Abstract

The asymmetric ring opening reactions of oxabenzonorbornadienes with carboxylic acids are described. By using the complex of [Rh(COD)Cl]₂and (S,S)-BDPP, with ZnI₂as the co-catalyst, a range of aromatic acids and alkyl acids were utilized as nucleophiles to afford the corresponding chiral hydronaphthalene products with high enantioselectivities (84–94% ee). Thus, the present methodology has provides an effective synthetic method for the preparation of enantioenriched hydronaphthalenes.

Original language	English
Pages (from-to)	62-68
Number of pages	7
Journal	Tetrahedron Asymmetry
Volume	28
Issue number	1
DOIs	https://doi.org/10.1016/j.tetasy.2016.11.004
Publication status	Published - 2017
Externally published	Yes

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title = "Rhodium/zinc co-catalyzed asymmetric ring opening reactions of oxabenzonorbornadienes with carboxylic acids",

abstract = "The asymmetric ring opening reactions of oxabenzonorbornadienes with carboxylic acids are described. By using the complex of [Rh(COD)Cl]2and (S,S)-BDPP, with ZnI2as the co-catalyst, a range of aromatic acids and alkyl acids were utilized as nucleophiles to afford the corresponding chiral hydronaphthalene products with high enantioselectivities (84–94\% ee). Thus, the present methodology has provides an effective synthetic method for the preparation of enantioenriched hydronaphthalenes.",

author = "Xiaobo He and Jingchao Chen and Xin Xu and Fan Yang and Cuiping Gu and Yongyun Zhou and Baomin Fan",

note = "Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd",

year = "2017",

doi = "10.1016/j.tetasy.2016.11.004",

language = "English",

volume = "28",

pages = "62--68",

journal = "Tetrahedron Asymmetry",

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T1 - Rhodium/zinc co-catalyzed asymmetric ring opening reactions of oxabenzonorbornadienes with carboxylic acids

AU - He, Xiaobo

AU - Chen, Jingchao

AU - Xu, Xin

AU - Yang, Fan

AU - Gu, Cuiping

AU - Zhou, Yongyun

AU - Fan, Baomin

PY - 2017

Y1 - 2017

N2 - The asymmetric ring opening reactions of oxabenzonorbornadienes with carboxylic acids are described. By using the complex of [Rh(COD)Cl]2and (S,S)-BDPP, with ZnI2as the co-catalyst, a range of aromatic acids and alkyl acids were utilized as nucleophiles to afford the corresponding chiral hydronaphthalene products with high enantioselectivities (84–94% ee). Thus, the present methodology has provides an effective synthetic method for the preparation of enantioenriched hydronaphthalenes.

AB - The asymmetric ring opening reactions of oxabenzonorbornadienes with carboxylic acids are described. By using the complex of [Rh(COD)Cl]2and (S,S)-BDPP, with ZnI2as the co-catalyst, a range of aromatic acids and alkyl acids were utilized as nucleophiles to afford the corresponding chiral hydronaphthalene products with high enantioselectivities (84–94% ee). Thus, the present methodology has provides an effective synthetic method for the preparation of enantioenriched hydronaphthalenes.

UR - http://www.scopus.com/inward/record.url?scp=85028246414&partnerID=8YFLogxK

U2 - 10.1016/j.tetasy.2016.11.004

DO - 10.1016/j.tetasy.2016.11.004

M3 - Article

AN - SCOPUS:85028246414

SN - 0957-4166

VL - 28

SP - 62

EP - 68

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 1

ER -

Rhodium/zinc co-catalyzed asymmetric ring opening reactions of oxabenzonorbornadienes with carboxylic acids

Abstract

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