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

doi:10.1016/S0040-4020(01)80808-5

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 journal › Article › peer-review

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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 language	English
Pages (from-to)	941-956
Journal	Tetrahedron
Volume	50
Issue number	3
DOIs	https://doi.org/10.1016/S0040-4020(01)80808-5
Publication status	Published - 1994

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

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.",

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

year = "1994",

doi = "10.1016/S0040-4020(01)80808-5",

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volume = "50",

pages = "941--956",

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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

IS - 3

ER -

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

Abstract

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