Exo Diastereoselective Diels-Alder Reactions of (R)-2-Phenyl-4-Methylene-Oxazolidin-5-one

S.G. Pyne, J. Safaei, D.C.R. Hockless, Brian Skelton, A.N. Sobolev, Allan White

Research output: Contribution to journalArticle

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Abstract

The thermally induced Diels-Alder reactions of (R)-2-phenyl-4-methylene-oxazolidin-5-one 2 and substituted 1,3-cyclohexadienes and substituted Ig-butadienes gives exo diastereomeric Diels-Alder adducts. In some cases the initially formed adducts undergo epimerization at the amino-acetal carbon, however the stereochemical integrity of the quaternary alpha-amino acid stereogenic centre is maintained and Diels-Alder adducts can be obtained in high enantiomeric purity (> 90% eel. The stereochemistry of these adducts has been elucidated by single crystal X-ray structure determinations and 2D H-1 NMR analysis.
Original languageEnglish
Pages (from-to)941-956
JournalTetrahedron
Volume50
Issue number3
DOIs
Publication statusPublished - 1994

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Butadienes
Oxazolidinones
Eels
Acetals
Stereochemistry
Cycloaddition Reaction
Carbon
Nuclear magnetic resonance
X-Rays
Single crystals
Amino Acids
X rays
1,3-cyclohexadiene

Cite this

Pyne, S.G. ; Safaei, J. ; Hockless, D.C.R. ; Skelton, Brian ; Sobolev, A.N. ; White, Allan. / Exo Diastereoselective Diels-Alder Reactions of (R)-2-Phenyl-4-Methylene-Oxazolidin-5-one. In: Tetrahedron. 1994 ; Vol. 50, No. 3. pp. 941-956.
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abstract = "The thermally induced Diels-Alder reactions of (R)-2-phenyl-4-methylene-oxazolidin-5-one 2 and substituted 1,3-cyclohexadienes and substituted Ig-butadienes gives exo diastereomeric Diels-Alder adducts. In some cases the initially formed adducts undergo epimerization at the amino-acetal carbon, however the stereochemical integrity of the quaternary alpha-amino acid stereogenic centre is maintained and Diels-Alder adducts can be obtained in high enantiomeric purity (> 90{\%} eel. The stereochemistry of these adducts has been elucidated by single crystal X-ray structure determinations and 2D H-1 NMR analysis.",
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Exo Diastereoselective Diels-Alder Reactions of (R)-2-Phenyl-4-Methylene-Oxazolidin-5-one. / Pyne, S.G.; Safaei, J.; Hockless, D.C.R.; Skelton, Brian; Sobolev, A.N.; White, Allan.

In: Tetrahedron, Vol. 50, No. 3, 1994, p. 941-956.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Exo Diastereoselective Diels-Alder Reactions of (R)-2-Phenyl-4-Methylene-Oxazolidin-5-one

AU - Pyne, S.G.

AU - Safaei, J.

AU - Hockless, D.C.R.

AU - Skelton, Brian

AU - Sobolev, A.N.

AU - White, Allan

PY - 1994

Y1 - 1994

N2 - The thermally induced Diels-Alder reactions of (R)-2-phenyl-4-methylene-oxazolidin-5-one 2 and substituted 1,3-cyclohexadienes and substituted Ig-butadienes gives exo diastereomeric Diels-Alder adducts. In some cases the initially formed adducts undergo epimerization at the amino-acetal carbon, however the stereochemical integrity of the quaternary alpha-amino acid stereogenic centre is maintained and Diels-Alder adducts can be obtained in high enantiomeric purity (> 90% eel. The stereochemistry of these adducts has been elucidated by single crystal X-ray structure determinations and 2D H-1 NMR analysis.

AB - The thermally induced Diels-Alder reactions of (R)-2-phenyl-4-methylene-oxazolidin-5-one 2 and substituted 1,3-cyclohexadienes and substituted Ig-butadienes gives exo diastereomeric Diels-Alder adducts. In some cases the initially formed adducts undergo epimerization at the amino-acetal carbon, however the stereochemical integrity of the quaternary alpha-amino acid stereogenic centre is maintained and Diels-Alder adducts can be obtained in high enantiomeric purity (> 90% eel. The stereochemistry of these adducts has been elucidated by single crystal X-ray structure determinations and 2D H-1 NMR analysis.

U2 - 10.1016/S0040-4020(01)80808-5

DO - 10.1016/S0040-4020(01)80808-5

M3 - Article

VL - 50

SP - 941

EP - 956

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

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