Synthesis of a constrained polyfunctional bicyclic iminocyclitol scaffold from l-sorbose via a tandem sequence including stereoselective intramolecular Huisgen cycloaddition

Ciaran O'Reilly; Colin O'Brien; Paul V. Murphy

doi:10.1016/j.tetlet.2009.05.060

Synthesis of a constrained polyfunctional bicyclic iminocyclitol scaffold from l-sorbose via a tandem sequence including stereoselective intramolecular Huisgen cycloaddition

Ciaran O'Reilly
, Colin O'Brien
, Paul V. Murphy

Infectious Disease

University College Dublin

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

9 Citations (Scopus)

Abstract

The synthesis of a functionalized (azido, amino, and hydroxy) 8-oxa-3-azabicyclo[3.2.1]octane framework and its conversion into a protected sugar amino acid and a tricyclic framework is described. The sequence includes a one-pot Huisgen 1,3-dipolar cycloaddition, with decomposition to an aziridine and subsequent ring opening by azide. The stereoselectivity observed in the Huisgen cycloaddition reaction is attributed to minimization of allylic strain.

Original language	English
Pages (from-to)	4427-4429
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	31
DOIs	https://doi.org/10.1016/j.tetlet.2009.05.060
Publication status	Published - 5 Aug 2009

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10.1016/j.tetlet.2009.05.060

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abstract = "The synthesis of a functionalized (azido, amino, and hydroxy) 8-oxa-3-azabicyclo[3.2.1]octane framework and its conversion into a protected sugar amino acid and a tricyclic framework is described. The sequence includes a one-pot Huisgen 1,3-dipolar cycloaddition, with decomposition to an aziridine and subsequent ring opening by azide. The stereoselectivity observed in the Huisgen cycloaddition reaction is attributed to minimization of allylic strain.",

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journal = "Tetrahedron Letters",

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Synthesis of a constrained polyfunctional bicyclic iminocyclitol scaffold from l-sorbose via a tandem sequence including stereoselective intramolecular Huisgen cycloaddition. / O'Reilly, Ciaran; O'Brien, Colin; Murphy, Paul V.
In: Tetrahedron Letters, Vol. 50, No. 31, 05.08.2009, p. 4427-4429.

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

TY - JOUR

T1 - Synthesis of a constrained polyfunctional bicyclic iminocyclitol scaffold from l-sorbose via a tandem sequence including stereoselective intramolecular Huisgen cycloaddition

AU - O'Reilly, Ciaran

AU - O'Brien, Colin

AU - Murphy, Paul V.

PY - 2009/8/5

Y1 - 2009/8/5

N2 - The synthesis of a functionalized (azido, amino, and hydroxy) 8-oxa-3-azabicyclo[3.2.1]octane framework and its conversion into a protected sugar amino acid and a tricyclic framework is described. The sequence includes a one-pot Huisgen 1,3-dipolar cycloaddition, with decomposition to an aziridine and subsequent ring opening by azide. The stereoselectivity observed in the Huisgen cycloaddition reaction is attributed to minimization of allylic strain.

AB - The synthesis of a functionalized (azido, amino, and hydroxy) 8-oxa-3-azabicyclo[3.2.1]octane framework and its conversion into a protected sugar amino acid and a tricyclic framework is described. The sequence includes a one-pot Huisgen 1,3-dipolar cycloaddition, with decomposition to an aziridine and subsequent ring opening by azide. The stereoselectivity observed in the Huisgen cycloaddition reaction is attributed to minimization of allylic strain.

UR - https://www.scopus.com/pages/publications/66949120720

U2 - 10.1016/j.tetlet.2009.05.060

DO - 10.1016/j.tetlet.2009.05.060

M3 - Article

SN - 0040-4039

VL - 50

SP - 4427

EP - 4429

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 31

ER -

Synthesis of a constrained polyfunctional bicyclic iminocyclitol scaffold from l-sorbose via a tandem sequence including stereoselective intramolecular Huisgen cycloaddition

Abstract

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