Publication:
Asymmetric Diels-Alder reactions of N-allenoyloxazolidinones catalyzed by Cu(II)-bis(oxazoline) complexes

Issued Date

2014-12-10

Resource Type

Article

ISSN

18733581
00404039

DOI

10.1016/j.tetlet.2014.10.051

Other identifier(s)

2-s2.0-84910678550

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Tetrahedron Letters. Vol.55, No.50 (2014), 6803-6807

Suggested Citation

Torsak Luanphaisarnnont Asymmetric Diels-Alder reactions of N-allenoyloxazolidinones catalyzed by Cu(II)-bis(oxazoline) complexes. Tetrahedron Letters. Vol.55, No.50 (2014), 6803-6807. doi:10.1016/j.tetlet.2014.10.051 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/33201

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Title

Asymmetric Diels-Alder reactions of N-allenoyloxazolidinones catalyzed by Cu(II)-bis(oxazoline) complexes

Author(s)

Torsak Luanphaisarnnont

Other Contributor(s)

Mahidol University

Abstract

© 2014 Elsevier Ltd. All rights reserved. Catalytic asymmetric Diels-Alder reactions of N-allenoyloxazolidinones were investigated. Various chiral metal-bis(oxazoline) and metal-pyridinebis(oxazoline) complexes were screened. Cu(SbF6)2(H2O)2(t-BuBox) was found to be the most effective catalyst, giving the product in high yield, enantioselectivity, and endo:exo selectivity. The relative reactivity between N-allenoyloxazolidinones and N-alkenoyloxazolidinones was also investigated. A model for stereoinduction was proposed to account for the enantioselectivity and endo:exo selectivity.

Keyword(s)

Biochemistry, Genetics and Molecular Biology
 Chemistry
 Pharmacology, Toxicology and Pharmaceutics

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https://repository.li.mahidol.ac.th/handle/20.500.14594/33201

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