Abstract
| Original language | English |
|---|---|
| Pages (from-to) | 1511-1533 |
| Journal | Australian Journal of Chemistry: an international journal for chemical science |
| Volume | 48 |
| DOIs | |
| Publication status | Published - 1995 |
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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 journal › Article
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 -