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

9 Scopus citations

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

Access to Document

10.1021/acs.orglett.0c01846

Cite this

@article{3cbfc95f4f3c4ba0b04d2fdee8e8489e,

title = "From Heterocycles to Carbacycles: Synthesis of Carbocyclic Nucleoside Analogues from Enals and Hydroxylamines",

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.",

author = "Pulakesh Das and Almond, {David W.} and Tumbelty, {Lauren N.} and Austin, {Brooke E.} and Gustavo Moura-Letts",

note = "Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = jul,

day = "17",

doi = "10.1021/acs.orglett.0c01846",

language = "English (US)",

volume = "22",

pages = "5491--5495",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "14",

}

TY - JOUR

T1 - From Heterocycles to Carbacycles

T2 - Synthesis of Carbocyclic Nucleoside Analogues from Enals and Hydroxylamines

AU - Das, Pulakesh

AU - Almond, David W.

AU - Tumbelty, Lauren N.

AU - Austin, Brooke E.

AU - Moura-Letts, Gustavo

PY - 2020/7/17

Y1 - 2020/7/17

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85087721987&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85087721987&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.0c01846

DO - 10.1021/acs.orglett.0c01846

M3 - Article

C2 - 32602726

AN - SCOPUS:85087721987

SN - 1523-7060

VL - 22

SP - 5491

EP - 5495

JO - Organic Letters

JF - Organic Letters

IS - 14

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this