Basic and reductive sulfone-directed ring-opening reactions of difluorinated oxa[2.2.1]bicycloheptanes

Patrick J Crowley, John Fawcett, Benson M Kariuki, Andrew C Moralee, Jonathan Percy, Vittoria Salafia

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Phenylsulfenyl chloride reacts with racemic endo Diels-Alder adduct 4 (DEC ) CONEt2) to afford lactone 8, which can be reduced and protected in a series of high-yielding steps. Key sulfone 10 can be ring opened under strong base conditions to afford vinyl sulfone 11. Attempted desulfonation resulted in the formation of a monofluoroalkene, but a direct desulfonation/eliminative ring opening with strain relief delivered highly functionalized monocyclic species 16.
LanguageEnglish
Pages4125-4128
Number of pages4
JournalOrganic Letters
Volume4
Issue number23
DOIs
Publication statusPublished - 2002

Fingerprint

Sulfones
sulfones
Lactones
Chlorides
rings
adducts
chlorides
divinyl sulfone

Keywords

  • strain relief
  • monofluoroalkene
  • ring opening

Cite this

Crowley, P. J., Fawcett, J., Kariuki, B. M., Moralee, A. C., Percy, J., & Salafia, V. (2002). Basic and reductive sulfone-directed ring-opening reactions of difluorinated oxa[2.2.1]bicycloheptanes. Organic Letters, 4(23), 4125-4128 . https://doi.org/10.1021/ol0268743
Crowley, Patrick J ; Fawcett, John ; Kariuki, Benson M ; Moralee, Andrew C ; Percy, Jonathan ; Salafia, Vittoria. / Basic and reductive sulfone-directed ring-opening reactions of difluorinated oxa[2.2.1]bicycloheptanes. In: Organic Letters. 2002 ; Vol. 4, No. 23. pp. 4125-4128 .
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abstract = "Phenylsulfenyl chloride reacts with racemic endo Diels-Alder adduct 4 (DEC ) CONEt2) to afford lactone 8, which can be reduced and protected in a series of high-yielding steps. Key sulfone 10 can be ring opened under strong base conditions to afford vinyl sulfone 11. Attempted desulfonation resulted in the formation of a monofluoroalkene, but a direct desulfonation/eliminative ring opening with strain relief delivered highly functionalized monocyclic species 16.",
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Crowley, PJ, Fawcett, J, Kariuki, BM, Moralee, AC, Percy, J & Salafia, V 2002, 'Basic and reductive sulfone-directed ring-opening reactions of difluorinated oxa[2.2.1]bicycloheptanes' Organic Letters, vol. 4, no. 23, pp. 4125-4128 . https://doi.org/10.1021/ol0268743

Basic and reductive sulfone-directed ring-opening reactions of difluorinated oxa[2.2.1]bicycloheptanes. / Crowley, Patrick J; Fawcett, John; Kariuki, Benson M; Moralee, Andrew C; Percy, Jonathan; Salafia, Vittoria.

In: Organic Letters, Vol. 4, No. 23, 2002, p. 4125-4128 .

Research output: Contribution to journalArticle

TY - JOUR

T1 - Basic and reductive sulfone-directed ring-opening reactions of difluorinated oxa[2.2.1]bicycloheptanes

AU - Crowley, Patrick J

AU - Fawcett, John

AU - Kariuki, Benson M

AU - Moralee, Andrew C

AU - Percy, Jonathan

AU - Salafia, Vittoria

PY - 2002

Y1 - 2002

N2 - Phenylsulfenyl chloride reacts with racemic endo Diels-Alder adduct 4 (DEC ) CONEt2) to afford lactone 8, which can be reduced and protected in a series of high-yielding steps. Key sulfone 10 can be ring opened under strong base conditions to afford vinyl sulfone 11. Attempted desulfonation resulted in the formation of a monofluoroalkene, but a direct desulfonation/eliminative ring opening with strain relief delivered highly functionalized monocyclic species 16.

AB - Phenylsulfenyl chloride reacts with racemic endo Diels-Alder adduct 4 (DEC ) CONEt2) to afford lactone 8, which can be reduced and protected in a series of high-yielding steps. Key sulfone 10 can be ring opened under strong base conditions to afford vinyl sulfone 11. Attempted desulfonation resulted in the formation of a monofluoroalkene, but a direct desulfonation/eliminative ring opening with strain relief delivered highly functionalized monocyclic species 16.

KW - strain relief

KW - monofluoroalkene

KW - ring opening

U2 - 10.1021/ol0268743

DO - 10.1021/ol0268743

M3 - Article

VL - 4

SP - 4125

EP - 4128

JO - Organic Letters

T2 - Organic Letters

JF - Organic Letters

SN - 1523-7060

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