Basic and reductive sulfone-directed ring-opening reactions of difluorinated oxa[2.21]bicycloheptanes

PJ Crowley; J Fawcett; Benson Kariuki; Andrew Moralee; Jonathan Percy; Vittoria Salafia

doi:10.1021/ol0268743

Basic and reductive sulfone-directed ring-opening reactions of difluorinated oxa[2.21]bicycloheptanes

PJ Crowley, J Fawcett, Benson Kariuki, Andrew Moralee, Jonathan Percy, Vittoria Salafia

Chemistry

Research output: Contribution to journal › Article

29 Citations (Scopus)

Abstract

Phenylsulfenyl chloride reacts with racemic endo Diels-Alder adduct 4 (DEC = CONEt(2)) 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. [reaction: see text]

Original language	English
Pages (from-to)	4125-4128
Number of pages	4
Journal	Organic Letters
Volume	4
DOIs	https://doi.org/10.1021/ol0268743
Publication status	Published - 1 Jan 2002

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title = "Basic and reductive sulfone-directed ring-opening reactions of difluorinated oxa[2.21]bicycloheptanes",

abstract = "Phenylsulfenyl chloride reacts with racemic endo Diels-Alder adduct 4 (DEC = CONEt(2)) 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. [reaction: see text]",

author = "PJ Crowley and J Fawcett and Benson Kariuki and Andrew Moralee and Jonathan Percy and Vittoria Salafia",

year = "2002",

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doi = "10.1021/ol0268743",

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T1 - Basic and reductive sulfone-directed ring-opening reactions of difluorinated oxa[2.21]bicycloheptanes

AU - Crowley, PJ

AU - Fawcett, J

AU - Kariuki, Benson

AU - Moralee, Andrew

AU - Percy, Jonathan

AU - Salafia, Vittoria

PY - 2002/1/1

Y1 - 2002/1/1

N2 - Phenylsulfenyl chloride reacts with racemic endo Diels-Alder adduct 4 (DEC = CONEt(2)) 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. [reaction: see text]

AB - Phenylsulfenyl chloride reacts with racemic endo Diels-Alder adduct 4 (DEC = CONEt(2)) 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. [reaction: see text]

UR - http://www.scopus.com/inward/record.url?scp=0042738074&partnerID=8YFLogxK

U2 - 10.1021/ol0268743

DO - 10.1021/ol0268743

M3 - Article

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VL - 4

SP - 4125

EP - 4128

JO - Organic Letters

JF - Organic Letters

ER -

Basic and reductive sulfone-directed ring-opening reactions of difluorinated oxa[2.21]bicycloheptanes

Abstract

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