Novel rearrangements of chiral 3-oxazolidinylazetidin-2-ones

Iwao Ojima; Yazhong Pei

doi:10.1016/S0040-4039(00)91567-3

Novel rearrangements of chiral 3-oxazolidinylazetidin-2-ones

Iwao Ojima
, Yazhong Pei

Chemistry

Stony Brook University

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

Reaction of a 3-oxazolininyl-4-hydroxymethylazetidin-2-one with excess NaOMe in refluxing methanol gives the corresponding 4-oxa-1,8-diazabicyclo[4.3.0]nonan-5,9-dione stereospecifically in nearly quantitative yield via a novel skeletal rearrangement, which includes a gamma-lactone as a key-intermediate; Possible mechanisms and similar rearrangement in a related system is discussed.

Original language	English
Pages (from-to)	887-890
Number of pages	4
Journal	Tetrahedron Letters
Volume	33
Issue number	7
DOIs	https://doi.org/10.1016/S0040-4039(00)91567-3
State	Published - Feb 11 1992

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title = "Novel rearrangements of chiral 3-oxazolidinylazetidin-2-ones",

abstract = "Reaction of a 3-oxazolininyl-4-hydroxymethylazetidin-2-one with excess NaOMe in refluxing methanol gives the corresponding 4-oxa-1,8-diazabicyclo[4.3.0]nonan-5,9-dione stereospecifically in nearly quantitative yield via a novel skeletal rearrangement, which includes a gamma-lactone as a key-intermediate; Possible mechanisms and similar rearrangement in a related system is discussed.",

author = "Iwao Ojima and Yazhong Pei",

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doi = "10.1016/S0040-4039(00)91567-3",

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journal = "Tetrahedron Letters",

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T1 - Novel rearrangements of chiral 3-oxazolidinylazetidin-2-ones

AU - Ojima, Iwao

AU - Pei, Yazhong

PY - 1992/2/11

Y1 - 1992/2/11

N2 - Reaction of a 3-oxazolininyl-4-hydroxymethylazetidin-2-one with excess NaOMe in refluxing methanol gives the corresponding 4-oxa-1,8-diazabicyclo[4.3.0]nonan-5,9-dione stereospecifically in nearly quantitative yield via a novel skeletal rearrangement, which includes a gamma-lactone as a key-intermediate; Possible mechanisms and similar rearrangement in a related system is discussed.

AB - Reaction of a 3-oxazolininyl-4-hydroxymethylazetidin-2-one with excess NaOMe in refluxing methanol gives the corresponding 4-oxa-1,8-diazabicyclo[4.3.0]nonan-5,9-dione stereospecifically in nearly quantitative yield via a novel skeletal rearrangement, which includes a gamma-lactone as a key-intermediate; Possible mechanisms and similar rearrangement in a related system is discussed.

UR - https://www.scopus.com/pages/publications/0026502649

U2 - 10.1016/S0040-4039(00)91567-3

DO - 10.1016/S0040-4039(00)91567-3

M3 - Article

AN - SCOPUS:0026502649

SN - 0040-4039

VL - 33

SP - 887

EP - 890

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 7

ER -

Novel rearrangements of chiral 3-oxazolidinylazetidin-2-ones

Abstract

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