Diasteroselective synthesis of oxazolidines and imidazolidines via the Lewis acid catalyzed C-C cleavage of aziridines

Zheng Jiang; Jing Wang; Ping Lu; Yanguang Wang

doi:10.1016/j.tet.2011.09.085

Diasteroselective synthesis of oxazolidines and imidazolidines via the Lewis acid catalyzed C-C cleavage of aziridines

Zheng Jiang, Jing Wang, Ping Lu^*, Yanguang Wang

^*Corresponding author for this work

Zhejiang University

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

37 Citations (Scopus)

Abstract

In this work, cis-2,5-disubstitutedoxazolidines were efficiently constructed via a regioselective C-C bond cleavage of N-tosylaziridine 2,2-dicaboxylates and a subsequent [3+2] cycloaddition with aromatic aldehydes in the presence of Zn(OTf)₂. The reactions were highly diastereoselective to form oxazolidines in cis configurations. trans-2,5-Disubstituted imidazolidines were also diastereoselectively synthesized in the similar manner using imines as substrates and AgOTf as catalyst. Based on the detailed investigation of the substrate diversity for both reactions, including the electronic effects and the steric effects of the substituted groups on the aziridines, aldehydes, and imines, a stepwise mechanism was postulated for the diastereoselective formation of cis-2,5-disubstitutedoxazolidines and trans-2,5-disubstituted imidazolines.

Original language	English
Pages (from-to)	9609-9617
Number of pages	9
Journal	Tetrahedron
Volume	67
Issue number	49
DOIs	https://doi.org/10.1016/j.tet.2011.09.085
Publication status	Published - 9 Dec 2011
Externally published	Yes

Keywords

Aziridines
Azomethine ylides
Cycloadditions
Imidazolidines
Oxazolines

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10.1016/j.tet.2011.09.085

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title = "Diasteroselective synthesis of oxazolidines and imidazolidines via the Lewis acid catalyzed C-C cleavage of aziridines",

abstract = "In this work, cis-2,5-disubstitutedoxazolidines were efficiently constructed via a regioselective C-C bond cleavage of N-tosylaziridine 2,2-dicaboxylates and a subsequent [3+2] cycloaddition with aromatic aldehydes in the presence of Zn(OTf)2. The reactions were highly diastereoselective to form oxazolidines in cis configurations. trans-2,5-Disubstituted imidazolidines were also diastereoselectively synthesized in the similar manner using imines as substrates and AgOTf as catalyst. Based on the detailed investigation of the substrate diversity for both reactions, including the electronic effects and the steric effects of the substituted groups on the aziridines, aldehydes, and imines, a stepwise mechanism was postulated for the diastereoselective formation of cis-2,5-disubstitutedoxazolidines and trans-2,5-disubstituted imidazolines.",

keywords = "Aziridines, Azomethine ylides, Cycloadditions, Imidazolidines, Oxazolines",

author = "Zheng Jiang and Jing Wang and Ping Lu and Yanguang Wang",

year = "2011",

month = dec,

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doi = "10.1016/j.tet.2011.09.085",

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T1 - Diasteroselective synthesis of oxazolidines and imidazolidines via the Lewis acid catalyzed C-C cleavage of aziridines

AU - Jiang, Zheng

AU - Wang, Jing

AU - Lu, Ping

AU - Wang, Yanguang

PY - 2011/12/9

Y1 - 2011/12/9

N2 - In this work, cis-2,5-disubstitutedoxazolidines were efficiently constructed via a regioselective C-C bond cleavage of N-tosylaziridine 2,2-dicaboxylates and a subsequent [3+2] cycloaddition with aromatic aldehydes in the presence of Zn(OTf)2. The reactions were highly diastereoselective to form oxazolidines in cis configurations. trans-2,5-Disubstituted imidazolidines were also diastereoselectively synthesized in the similar manner using imines as substrates and AgOTf as catalyst. Based on the detailed investigation of the substrate diversity for both reactions, including the electronic effects and the steric effects of the substituted groups on the aziridines, aldehydes, and imines, a stepwise mechanism was postulated for the diastereoselective formation of cis-2,5-disubstitutedoxazolidines and trans-2,5-disubstituted imidazolines.

AB - In this work, cis-2,5-disubstitutedoxazolidines were efficiently constructed via a regioselective C-C bond cleavage of N-tosylaziridine 2,2-dicaboxylates and a subsequent [3+2] cycloaddition with aromatic aldehydes in the presence of Zn(OTf)2. The reactions were highly diastereoselective to form oxazolidines in cis configurations. trans-2,5-Disubstituted imidazolidines were also diastereoselectively synthesized in the similar manner using imines as substrates and AgOTf as catalyst. Based on the detailed investigation of the substrate diversity for both reactions, including the electronic effects and the steric effects of the substituted groups on the aziridines, aldehydes, and imines, a stepwise mechanism was postulated for the diastereoselective formation of cis-2,5-disubstitutedoxazolidines and trans-2,5-disubstituted imidazolines.

KW - Aziridines

KW - Azomethine ylides

KW - Cycloadditions

KW - Imidazolidines

KW - Oxazolines

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U2 - 10.1016/j.tet.2011.09.085

DO - 10.1016/j.tet.2011.09.085

M3 - Article

AN - SCOPUS:80555150537

SN - 0040-4020

VL - 67

SP - 9609

EP - 9617

JO - Tetrahedron

JF - Tetrahedron

IS - 49

ER -

Diasteroselective synthesis of oxazolidines and imidazolidines via the Lewis acid catalyzed C-C cleavage of aziridines

Abstract

Keywords

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