1,3-Dipolar cycloadditions of a chiral oxazolidinone with nitrones and nitrile oxides

S.G. Pyne, J. Safaei-G, Brian Skelton, Allan White

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

The 1,3-dipolar cycloaddition reactions of the chiral oxazolidinone (1) and nitrones are highly regioselective and only 5,5-disubstituted isoxazolidine adducts are formed. These reactions occur under equilibrating conditions to give the more stable adducts that result from addition to the exocyclic methylene of (1) from the sterically more hindered pi-face. The endo adducts are generally thermodynamically favoured. In one case the novel azetidine (21) was formed from the treatment of the adduct (4a) with palladium hydroxide on carbon under a hydrogen atmosphere. The major adducts from the reaction of (1) and nitrile oxides (16a,b) had the expected stereochemistry, addition of the 1,3-dipole having occurred from the less hindered pi-face of the exocyclic methylene of (1). The stereochemistry of many of these products has been elucidated by single-crystal X-ray structural determinations.
Original languageEnglish
Pages (from-to)1511-1533
JournalAustralian Journal of Chemistry: an international journal for chemical science
Volume48
DOIs
Publication statusPublished - 1995

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Oxazolidinones
Nitriles
Stereochemistry
Cycloaddition
Oxides
Palladium
Hydrogen
Carbon
Single crystals
X rays
nitrones
hydroxide ion
azetidine

Cite this

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title = "1,3-Dipolar cycloadditions of a chiral oxazolidinone with nitrones and nitrile oxides",
abstract = "The 1,3-dipolar cycloaddition reactions of the chiral oxazolidinone (1) and nitrones are highly regioselective and only 5,5-disubstituted isoxazolidine adducts are formed. These reactions occur under equilibrating conditions to give the more stable adducts that result from addition to the exocyclic methylene of (1) from the sterically more hindered pi-face. The endo adducts are generally thermodynamically favoured. In one case the novel azetidine (21) was formed from the treatment of the adduct (4a) with palladium hydroxide on carbon under a hydrogen atmosphere. The major adducts from the reaction of (1) and nitrile oxides (16a,b) had the expected stereochemistry, addition of the 1,3-dipole having occurred from the less hindered pi-face of the exocyclic methylene of (1). The stereochemistry of many of these products has been elucidated by single-crystal X-ray structural determinations.",
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journal = "Australian Journal of Chemistry:an international journal for chemical science",
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1,3-Dipolar cycloadditions of a chiral oxazolidinone with nitrones and nitrile oxides. / Pyne, S.G.; Safaei-G, J.; Skelton, Brian; White, Allan.

In: Australian Journal of Chemistry: an international journal for chemical science, Vol. 48, 1995, p. 1511-1533.

Research output: Contribution to journalArticle

TY - JOUR

T1 - 1,3-Dipolar cycloadditions of a chiral oxazolidinone with nitrones and nitrile oxides

AU - Pyne, S.G.

AU - Safaei-G, J.

AU - Skelton, Brian

AU - White, Allan

PY - 1995

Y1 - 1995

N2 - The 1,3-dipolar cycloaddition reactions of the chiral oxazolidinone (1) and nitrones are highly regioselective and only 5,5-disubstituted isoxazolidine adducts are formed. These reactions occur under equilibrating conditions to give the more stable adducts that result from addition to the exocyclic methylene of (1) from the sterically more hindered pi-face. The endo adducts are generally thermodynamically favoured. In one case the novel azetidine (21) was formed from the treatment of the adduct (4a) with palladium hydroxide on carbon under a hydrogen atmosphere. The major adducts from the reaction of (1) and nitrile oxides (16a,b) had the expected stereochemistry, addition of the 1,3-dipole having occurred from the less hindered pi-face of the exocyclic methylene of (1). The stereochemistry of many of these products has been elucidated by single-crystal X-ray structural determinations.

AB - The 1,3-dipolar cycloaddition reactions of the chiral oxazolidinone (1) and nitrones are highly regioselective and only 5,5-disubstituted isoxazolidine adducts are formed. These reactions occur under equilibrating conditions to give the more stable adducts that result from addition to the exocyclic methylene of (1) from the sterically more hindered pi-face. The endo adducts are generally thermodynamically favoured. In one case the novel azetidine (21) was formed from the treatment of the adduct (4a) with palladium hydroxide on carbon under a hydrogen atmosphere. The major adducts from the reaction of (1) and nitrile oxides (16a,b) had the expected stereochemistry, addition of the 1,3-dipole having occurred from the less hindered pi-face of the exocyclic methylene of (1). The stereochemistry of many of these products has been elucidated by single-crystal X-ray structural determinations.

U2 - 10.1071/CH9951511

DO - 10.1071/CH9951511

M3 - Article

VL - 48

SP - 1511

EP - 1533

JO - Australian Journal of Chemistry:an international journal for chemical science

JF - Australian Journal of Chemistry:an international journal for chemical science

SN - 0004-9425

ER -