From Heterocycles to Carbacycles: Synthesis of Carbocyclic Nucleoside Analogues from Enals and Hydroxylamines

Pulakesh Das, David W. Almond, Lauren N. Tumbelty, Brooke E. Austin, Gustavo Moura-Letts

Research output: Contribution to journalArticlepeer-review

Abstract

Substituted and stereochemically dense carbacycles can be prepared by sequential dipolar cycloaddition and reductive cleavage from enals and hydroxylamines. The reaction sequence proceeds with high efficiency for a wide variety of enals and hydroxylamines. The reaction is regio- and diastereoselective for the initial formation of a bridged bisisoxazolidine intermediate, which then undergoes quantitative double N-O cleavage to produce carbacycles as single diastereomers.

Original languageEnglish (US)
Pages (from-to)5491-5495
Number of pages5
JournalOrganic Letters
Volume22
Issue number14
DOIs
StatePublished - Jul 17 2020

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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