Enantioselective Ring Opening Reactions of Azabenzonorbornadienes with Carboxylic Acids

Yongyun Zhou; Cuiping Gu; Jingchao Chen; Meina Zhu; Fan Yang; Jianbin Xu; Baomin Fan

doi:10.1002/adsc.201600520

Enantioselective Ring Opening Reactions of Azabenzonorbornadienes with Carboxylic Acids

Yongyun Zhou, Cuiping Gu, Jingchao Chen, Meina Zhu, Fan Yang, Jianbin Xu, Baomin Fan^*

^*Corresponding author for this work

Yunnan Minzu University

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

15 Citations (Scopus)

Abstract

The palladium/silver (Pd/Ag) co-catalytic system was found to be effective for the enantioselective ring opening reactions of the low reactive azabenzonorbornadienes with weak nucleophilic carboxylic acids. Both aryl and alkyl carboxylic acids are suitable nucleophiles and afforded the cis ring opening products in good yields with excellent enantioselectivities. The absolute configuration of one of the products has been confirmed by X-ray crystal structure analysis, and a plausible reaction pathway is proposed. (Figure presented.).

Original language	English
Pages (from-to)	3167-3172
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	358
Issue number	20
DOIs	https://doi.org/10.1002/adsc.201600520
Publication status	Published - 20 Oct 2016
Externally published	Yes

Keywords

asymmetric synthesis
azabenzonorbornadienes
carboxylic acids
co-catalysts
ring opening reaction

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10.1002/adsc.201600520

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abstract = "The palladium/silver (Pd/Ag) co-catalytic system was found to be effective for the enantioselective ring opening reactions of the low reactive azabenzonorbornadienes with weak nucleophilic carboxylic acids. Both aryl and alkyl carboxylic acids are suitable nucleophiles and afforded the cis ring opening products in good yields with excellent enantioselectivities. The absolute configuration of one of the products has been confirmed by X-ray crystal structure analysis, and a plausible reaction pathway is proposed. (Figure presented.).",

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author = "Yongyun Zhou and Cuiping Gu and Jingchao Chen and Meina Zhu and Fan Yang and Jianbin Xu and Baomin Fan",

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T1 - Enantioselective Ring Opening Reactions of Azabenzonorbornadienes with Carboxylic Acids

AU - Zhou, Yongyun

AU - Gu, Cuiping

AU - Chen, Jingchao

AU - Zhu, Meina

AU - Yang, Fan

AU - Xu, Jianbin

AU - Fan, Baomin

PY - 2016/10/20

Y1 - 2016/10/20

N2 - The palladium/silver (Pd/Ag) co-catalytic system was found to be effective for the enantioselective ring opening reactions of the low reactive azabenzonorbornadienes with weak nucleophilic carboxylic acids. Both aryl and alkyl carboxylic acids are suitable nucleophiles and afforded the cis ring opening products in good yields with excellent enantioselectivities. The absolute configuration of one of the products has been confirmed by X-ray crystal structure analysis, and a plausible reaction pathway is proposed. (Figure presented.).

AB - The palladium/silver (Pd/Ag) co-catalytic system was found to be effective for the enantioselective ring opening reactions of the low reactive azabenzonorbornadienes with weak nucleophilic carboxylic acids. Both aryl and alkyl carboxylic acids are suitable nucleophiles and afforded the cis ring opening products in good yields with excellent enantioselectivities. The absolute configuration of one of the products has been confirmed by X-ray crystal structure analysis, and a plausible reaction pathway is proposed. (Figure presented.).

KW - asymmetric synthesis

KW - azabenzonorbornadienes

KW - carboxylic acids

KW - co-catalysts

KW - ring opening reaction

UR - http://www.scopus.com/inward/record.url?scp=84991272174&partnerID=8YFLogxK

U2 - 10.1002/adsc.201600520

DO - 10.1002/adsc.201600520

M3 - Article

AN - SCOPUS:84991272174

SN - 1615-4150

VL - 358

SP - 3167

EP - 3172

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 20

ER -

Enantioselective Ring Opening Reactions of Azabenzonorbornadienes with Carboxylic Acids

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