Partial Racemization Occurring in the Hydroxylactonization of a δ,ε-Epoxy Amide

Masaru ENOMOTO; Shigefumi KUWAHARA

doi:10.1271/bbb.100646

Bioscience, Biotechnology, and Biochemistry

Online ISSN : 1347-6947
Print ISSN : 0916-8451

Organic Chemistry Notes

Partial Racemization Occurring in the Hydroxylactonization of a δ,ε-Epoxy Amide

Masaru ENOMOTO, Shigefumi KUWAHARA

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Keywords: dihydroisocoumarin, epoxy amide, hydroxylactonization, racemization, Baldwin rule

JOURNAL FREE ACCESS

2010 Volume 74 Issue 12 Pages 2535-2537

DOI https://doi.org/10.1271/bbb.100646

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Abstract

Acid-promoted hydroxylactonization of a δ,ε-epoxy amide took place via both 6-exo-tet and 7-endo-tet processes, causing a considerable degree of racemization of the resulting δ-hydroxyalkyl-δ-lactone.

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