The use of Mosher derivatives for the determination of the absolute configuration of substituted isoxazolidines

Wentian Wang, Ryan T. Cassell, Kathleen S. Rein

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Isoxazolidines serve as intermediates in the synthesis of natural products. In addition, they can display significant biological activity, much of which derives from their ability to act as nucleoside analogues. As a result, considerable effort has been applied toward the asymmetric synthesis of isoxazolidines. However, a rapid and straightforward method for determination of the absolute configuration of isoxazolidines has not yet been reported. Herein we report the application of Mosher derivatives for the determination of the absolute configuration of substituted isoxazolidines. The Mosher derivatives exhibit conformational behavior similar to the Mosher derivatives of cyclic secondary amines. Interpretation of the chemical shift anisotropy, with these conformational biases in mind, can be used for the assignment of the absolute configuration of substituted isoxazolidines.

Original languageEnglish (US)
Pages (from-to)223-228
Number of pages6
JournalTetrahedron Asymmetry
Volume24
Issue number4
DOIs
StatePublished - Feb 28 2013
Externally publishedYes

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Derivatives
configurations
nucleosides
Chemical shift
synthesis
activity (biology)
Bioactivity
Biological Products
Nucleosides
Amines
chemical equilibrium
amines
Anisotropy
analogs
anisotropy
products

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

The use of Mosher derivatives for the determination of the absolute configuration of substituted isoxazolidines. / Wang, Wentian; Cassell, Ryan T.; Rein, Kathleen S.

In: Tetrahedron Asymmetry, Vol. 24, No. 4, 28.02.2013, p. 223-228.

Research output: Contribution to journalArticle

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