Vinyl sulfones in solid-phase synthesis: Preparation of 4,5,6,7-tetrahydroisoindole derivatives

W. C. Cheng; M. M. Olmstead; M. J. Kurth

doi:10.1021/jo0156823

Vinyl sulfones in solid-phase synthesis: Preparation of 4,5,6,7-tetrahydroisoindole derivatives

W. C. Cheng, M. M. Olmstead, M. J. Kurth

Chemistry

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

39 Scopus citations

Abstract

The preparation of functionalized 4,5,6,7-tetrahydroisoindole via a traceless solid-phase sulfone linker strategy is described. Thermolytic extrusion of SO₂ from polymer-bound 3-(phenylsulfonyl)-3-sulfolene (7) generated polymer-bound 2-(phenylsulfonyl)-1,3-butadiene (9) in situ which underwent Diels-Alder cycloaddition with various dienophiles to furnish vinyl sulfone resins 10-14. To complete a traceless linker cleavage strategy, (p-tolysulfonyl)methyl isocyanide or ethyl isocyanoacetate was employed to react with the vinyl sulfone moiety to liberate functionalized 4,5,6,7-tetrahydroisoindole products from the resin. Using this chemistry, nine tetrahydroisoindole derivatives (6, 15-22) were prepared in 32-41% overall yields from polystyrene/divinylbenzene sulfinate 1.

Original language	English (US)
Pages (from-to)	5528-5533
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	66
Issue number	16
DOIs	https://doi.org/10.1021/jo0156823
State	Published - Aug 10 2001

ASJC Scopus subject areas

Organic Chemistry

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title = "Vinyl sulfones in solid-phase synthesis: Preparation of 4,5,6,7-tetrahydroisoindole derivatives",

abstract = "The preparation of functionalized 4,5,6,7-tetrahydroisoindole via a traceless solid-phase sulfone linker strategy is described. Thermolytic extrusion of SO2 from polymer-bound 3-(phenylsulfonyl)-3-sulfolene (7) generated polymer-bound 2-(phenylsulfonyl)-1,3-butadiene (9) in situ which underwent Diels-Alder cycloaddition with various dienophiles to furnish vinyl sulfone resins 10-14. To complete a traceless linker cleavage strategy, (p-tolysulfonyl)methyl isocyanide or ethyl isocyanoacetate was employed to react with the vinyl sulfone moiety to liberate functionalized 4,5,6,7-tetrahydroisoindole products from the resin. Using this chemistry, nine tetrahydroisoindole derivatives (6, 15-22) were prepared in 32-41% overall yields from polystyrene/divinylbenzene sulfinate 1.",

author = "Cheng, {W. C.} and Olmstead, {M. M.} and Kurth, {M. J.}",

year = "2001",

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doi = "10.1021/jo0156823",

language = "English (US)",

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pages = "5528--5533",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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T1 - Vinyl sulfones in solid-phase synthesis

T2 - Preparation of 4,5,6,7-tetrahydroisoindole derivatives

AU - Cheng, W. C.

AU - Olmstead, M. M.

AU - Kurth, M. J.

PY - 2001/8/10

Y1 - 2001/8/10

N2 - The preparation of functionalized 4,5,6,7-tetrahydroisoindole via a traceless solid-phase sulfone linker strategy is described. Thermolytic extrusion of SO2 from polymer-bound 3-(phenylsulfonyl)-3-sulfolene (7) generated polymer-bound 2-(phenylsulfonyl)-1,3-butadiene (9) in situ which underwent Diels-Alder cycloaddition with various dienophiles to furnish vinyl sulfone resins 10-14. To complete a traceless linker cleavage strategy, (p-tolysulfonyl)methyl isocyanide or ethyl isocyanoacetate was employed to react with the vinyl sulfone moiety to liberate functionalized 4,5,6,7-tetrahydroisoindole products from the resin. Using this chemistry, nine tetrahydroisoindole derivatives (6, 15-22) were prepared in 32-41% overall yields from polystyrene/divinylbenzene sulfinate 1.

AB - The preparation of functionalized 4,5,6,7-tetrahydroisoindole via a traceless solid-phase sulfone linker strategy is described. Thermolytic extrusion of SO2 from polymer-bound 3-(phenylsulfonyl)-3-sulfolene (7) generated polymer-bound 2-(phenylsulfonyl)-1,3-butadiene (9) in situ which underwent Diels-Alder cycloaddition with various dienophiles to furnish vinyl sulfone resins 10-14. To complete a traceless linker cleavage strategy, (p-tolysulfonyl)methyl isocyanide or ethyl isocyanoacetate was employed to react with the vinyl sulfone moiety to liberate functionalized 4,5,6,7-tetrahydroisoindole products from the resin. Using this chemistry, nine tetrahydroisoindole derivatives (6, 15-22) were prepared in 32-41% overall yields from polystyrene/divinylbenzene sulfinate 1.

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