Article
From Heterocycles to Carbacycles: Synthesis of Carbocyclic Nucleoside Analogues from Enals and Hydroxylamines.
Organic Letters
(2020)
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.
Disciplines
Publication Date
June 30, 2020
DOI
10.1021/ACS.ORGLETT.0C01846
Citation Information
Pulakesh Das, David W. Almond, Lauren N. Tumbelty, Brooke E. Austin, et al.. "From Heterocycles to Carbacycles: Synthesis of Carbocyclic Nucleoside Analogues from Enals and Hydroxylamines." Organic Letters Vol. 22 Iss. 14 (2020) p. 5491 - 5495 Available at: http://works.bepress.com/gustavo-moura-letts/14/