Alkenylazaarenes as dipolarophiles in 1,3-dipolar cycloaddition of nitrones: Regioselectivity-switchable and highly diastereoselective synthesis of multisubstituted isoxazolidines

Mengchao Tong; Yong Zhang; Cong Qin; Yiwei Fu; Yonghai Liu; Hao Li; Wei Wang

doi:10.1039/c8qo00826d

Alkenylazaarenes as dipolarophiles in 1,3-dipolar cycloaddition of nitrones: Regioselectivity-switchable and highly diastereoselective synthesis of multisubstituted isoxazolidines

Mengchao Tong
, Yong Zhang
, Cong Qin
, Yiwei Fu
, Yonghai Liu
, Hao Li
, Wei Wang

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

19 Scopus citations

Abstract

Alkenylazaarenes as a novel class of dipolarophiles for 1,3-dipolar cycloaddition (1,3-DC) with nitrones was reported. A regioselectivity-switchable synthesis of multisubstituted isoxazolidines had been developed. In the presence of TMSOTf as catalyst, 4-substituted isoxazolidines were obtained as major products with high regio- and diastereoselectivities. Nonetheless, under microwave irradiation in a sealed system with water as solvent, exclusive 5-substituted isoxazolidines were produced in good yields.

Original language	English (US)
Pages (from-to)	2945-2949
Number of pages	5
Journal	Organic Chemistry Frontiers
Volume	5
Issue number	20
DOIs	https://doi.org/10.1039/c8qo00826d
State	Published - Oct 21 2018
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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Alkenylazaarenes as dipolarophiles in 1,3-dipolar cycloaddition of nitrones: Regioselectivity-switchable and highly diastereoselective synthesis of multisubstituted isoxazolidines. / Tong, Mengchao; Zhang, Yong; Qin, Cong et al.
In: Organic Chemistry Frontiers, Vol. 5, No. 20, 21.10.2018, p. 2945-2949.

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

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abstract = "Alkenylazaarenes as a novel class of dipolarophiles for 1,3-dipolar cycloaddition (1,3-DC) with nitrones was reported. A regioselectivity-switchable synthesis of multisubstituted isoxazolidines had been developed. In the presence of TMSOTf as catalyst, 4-substituted isoxazolidines were obtained as major products with high regio- and diastereoselectivities. Nonetheless, under microwave irradiation in a sealed system with water as solvent, exclusive 5-substituted isoxazolidines were produced in good yields.",

author = "Mengchao Tong and Yong Zhang and Cong Qin and Yiwei Fu and Yonghai Liu and Hao Li and Wei Wang",

note = "Funding Information: This work was supported by the National Natural Science Foundation of China (21572055, 21738002 and 21572054), the program for Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning, the Fundamental Research Funds for the Central Universities and the China 111 Project (Grant B07023). Publisher Copyright: {\textcopyright} the Partner Organisations.",

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AU - Tong, Mengchao

AU - Zhang, Yong

AU - Qin, Cong

AU - Fu, Yiwei

AU - Liu, Yonghai

AU - Li, Hao

AU - Wang, Wei

N1 - Funding Information: This work was supported by the National Natural Science Foundation of China (21572055, 21738002 and 21572054), the program for Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning, the Fundamental Research Funds for the Central Universities and the China 111 Project (Grant B07023). Publisher Copyright: © the Partner Organisations.

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AB - Alkenylazaarenes as a novel class of dipolarophiles for 1,3-dipolar cycloaddition (1,3-DC) with nitrones was reported. A regioselectivity-switchable synthesis of multisubstituted isoxazolidines had been developed. In the presence of TMSOTf as catalyst, 4-substituted isoxazolidines were obtained as major products with high regio- and diastereoselectivities. Nonetheless, under microwave irradiation in a sealed system with water as solvent, exclusive 5-substituted isoxazolidines were produced in good yields.

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Alkenylazaarenes as dipolarophiles in 1,3-dipolar cycloaddition of nitrones: Regioselectivity-switchable and highly diastereoselective synthesis of multisubstituted isoxazolidines

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