Asymmetric ring-opening reactions of azabenzonorbornadienes through transfer hydrogenation using secondary amines as hydrogen sources: Tuning of absolute configuration by acids

Dongdong Pu; Yongyun Zhou; Fan Yang; Guoli Shen; Yang Gao; Weiqing Sun; Ruhima Khan; Baomin Fan

doi:10.1039/c7qo01163f

Asymmetric ring-opening reactions of azabenzonorbornadienes through transfer hydrogenation using secondary amines as hydrogen sources: Tuning of absolute configuration by acids

Dongdong Pu, Yongyun Zhou^*, Fan Yang, Guoli Shen, Yang Gao, Weiqing Sun, Ruhima Khan, Baomin Fan

^*Corresponding author for this work

Yunnan Minzu University

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

14 Citations (Scopus)

Abstract

Reductive transfer hydrogenation of bicyclic alkenes has been developed under the co-catalytic system of palladium and silver by using secondary amines as reductants. The reaction results in the asymmetric ring-opening product. A wide range of azabenzonorbornadienes reacted well giving 1,2-dihydronaphthalen-1-amine derivatives in high yields with good enantioselectivities. The control of the absolute configuration of the product by addition of carboxylic acids has been demonstrated.

Original language	English
Pages (from-to)	3077-3082
Number of pages	6
Journal	Organic Chemistry Frontiers
Volume	5
Issue number	21
DOIs	https://doi.org/10.1039/c7qo01163f
Publication status	Published - 7 Nov 2018
Externally published	Yes

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Pu, D., Zhou, Y., Yang, F., Shen, G., Gao, Y., Sun, W., Khan, R., & Fan, B. (2018). Asymmetric ring-opening reactions of azabenzonorbornadienes through transfer hydrogenation using secondary amines as hydrogen sources: Tuning of absolute configuration by acids. Organic Chemistry Frontiers, 5(21), 3077-3082. https://doi.org/10.1039/c7qo01163f

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abstract = "Reductive transfer hydrogenation of bicyclic alkenes has been developed under the co-catalytic system of palladium and silver by using secondary amines as reductants. The reaction results in the asymmetric ring-opening product. A wide range of azabenzonorbornadienes reacted well giving 1,2-dihydronaphthalen-1-amine derivatives in high yields with good enantioselectivities. The control of the absolute configuration of the product by addition of carboxylic acids has been demonstrated.",

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AU - Pu, Dongdong

AU - Zhou, Yongyun

AU - Yang, Fan

AU - Shen, Guoli

AU - Gao, Yang

AU - Sun, Weiqing

AU - Khan, Ruhima

AU - Fan, Baomin

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N2 - Reductive transfer hydrogenation of bicyclic alkenes has been developed under the co-catalytic system of palladium and silver by using secondary amines as reductants. The reaction results in the asymmetric ring-opening product. A wide range of azabenzonorbornadienes reacted well giving 1,2-dihydronaphthalen-1-amine derivatives in high yields with good enantioselectivities. The control of the absolute configuration of the product by addition of carboxylic acids has been demonstrated.

AB - Reductive transfer hydrogenation of bicyclic alkenes has been developed under the co-catalytic system of palladium and silver by using secondary amines as reductants. The reaction results in the asymmetric ring-opening product. A wide range of azabenzonorbornadienes reacted well giving 1,2-dihydronaphthalen-1-amine derivatives in high yields with good enantioselectivities. The control of the absolute configuration of the product by addition of carboxylic acids has been demonstrated.

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Asymmetric ring-opening reactions of azabenzonorbornadienes through transfer hydrogenation using secondary amines as hydrogen sources: Tuning of absolute configuration by acids

Abstract

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