Publication:
Oxiranyl remote anions from epoxy cinnamates and their application towards the synthesis of α,β-epoxy-γ-butyrolactones

5

Issued Date

2020-12-10

Resource Type

Article

ISSN

18733581
00404039

DOI

10.1016/j.tetlet.2020.152609

Other identifier(s)

2-s2.0-85096084282

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Tetrahedron Letters. Vol.61, No.50 (2020)

Suggested Citation

Patpanat Sermmai, Nopporn Ruangsupapichat, Tienthong Thongpanchang Oxiranyl remote anions from epoxy cinnamates and their application towards the synthesis of α,β-epoxy-γ-butyrolactones. Tetrahedron Letters. Vol.61, No.50 (2020). doi:10.1016/j.tetlet.2020.152609 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/60381

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Title

Oxiranyl remote anions from epoxy cinnamates and their application towards the synthesis of α,β-epoxy-γ-butyrolactones

Author(s)

Patpanat Sermmai
 Nopporn Ruangsupapichat
 Tienthong Thongpanchang

Other Contributor(s)

Mahidol University

Abstract

© 2020 Elsevier Ltd A series of α,β-epoxy-γ-butyrolactones were synthesized in moderate yields via oxiranyl remote anions derived from epoxy cinnamate esters. The key synthetic step involved deprotonation of the β-position of α,β-epoxy cinnamate derivatives where the generated β-anion was stabilized by remote chelation from an ester group. The substitution reaction of the anion with a variety of ketones, followed by cyclization, readily furnished the desired substituted α,β-epoxy-γ-butyrolactones.

Keyword(s)

Biochemistry, Genetics and Molecular Biology
 Chemistry

Availability

URI

https://repository.li.mahidol.ac.th/handle/123456789/60381

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Scopus 2020