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

doi:10.1021/acs.orglett.0c01846

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

Chemistry

Research output: Contribution to journal › Article › peer-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 language	English (US)
Pages (from-to)	5491-5495
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	14
DOIs	https://doi.org/10.1021/acs.orglett.0c01846
State	Published - Jul 17 2020

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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.",

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AU - Almond, David W.

AU - Tumbelty, Lauren N.

AU - Austin, Brooke E.

AU - Moura-Letts, Gustavo

PY - 2020/7/17

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