An unusual oxidative rearrangement of azabicyclo[2.2.1]heptenes, providing a stereoselective route to 2'- and 3'-hydroxycyclopentylglycines

P. D. Bailey, I. M. McDonald, G. M. Rosair, D. Taylor

Research output: Contribution to journalArticle

Abstract

Treatment of the azabicyclo[2.2.1]heptene derivative 4 with mCPBA for 3-5 seconds generates the oxazabicyclo[3.2.1]octene derivative 7 (X-ray structure) via rapid Meisenheimer rearrangement of the N-oxide 5, whilst heating 7 in MeCN for 4-6 h leads to further rearrangement to the more thermodynamically stable oxazabicyclo[3.3.0]octene isomer 6; 6 and 7 can be readily reduced to enantio-pure hydroxylated cyclopentylglycine derivatives.

Original languageEnglish
Pages (from-to)2451-2452
Number of pages2
JournalChemical Communications
Issue number24
DOIs
Publication statusPublished - 21 Dec 2000

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Derivatives
Isomers
Oxides
Heating
X rays

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abstract = "Treatment of the azabicyclo[2.2.1]heptene derivative 4 with mCPBA for 3-5 seconds generates the oxazabicyclo[3.2.1]octene derivative 7 (X-ray structure) via rapid Meisenheimer rearrangement of the N-oxide 5, whilst heating 7 in MeCN for 4-6 h leads to further rearrangement to the more thermodynamically stable oxazabicyclo[3.3.0]octene isomer 6; 6 and 7 can be readily reduced to enantio-pure hydroxylated cyclopentylglycine derivatives.",
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publisher = "Royal Society of Chemistry",
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An unusual oxidative rearrangement of azabicyclo[2.2.1]heptenes, providing a stereoselective route to 2'- and 3'-hydroxycyclopentylglycines. / Bailey, P. D.; McDonald, I. M.; Rosair, G. M.; Taylor, D.

In: Chemical Communications, No. 24, 21.12.2000, p. 2451-2452.

Research output: Contribution to journalArticle

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AU - Bailey, P. D.

AU - McDonald, I. M.

AU - Rosair, G. M.

AU - Taylor, D.

PY - 2000/12/21

Y1 - 2000/12/21

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