Syntheses of 3,4-disubstituted pyrroles and furans via Lewis acid-promoted semipinacol rearrangement/alkyne-ketone metathesis reaction of (C)-2- N - Or O-((3-arylpropargyl)methyl)-tethered 3,5,5-trimethyl-2,3-epoxycyclohexan-1-ones

Ming Chang P. Yeh; Ming Nan Lin; Ching Hsien Hsu; Chia Jung Liang

doi:10.1021/jo402025z

Syntheses of 3,4-disubstituted pyrroles and furans via Lewis acid-promoted semipinacol rearrangement/alkyne-ketone metathesis reaction of (C)-2- N - Or O-((3-arylpropargyl)methyl)-tethered 3,5,5-trimethyl-2,3-epoxycyclohexan-1-ones

Ming Chang P. Yeh^*, Ming Nan Lin, Ching Hsien Hsu, Chia Jung Liang

^*Corresponding author for this work

Department of Chemistry

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

26 Citations (Scopus)

Abstract

The synthesis of 2,3-disubstituted pyrroles via TMSOTf-assisted cyclization reaction of 3,5,5-trimethyl-2,3-epoxycyclohexan-1-ones incorporating a (3-arylpropargyltosylamino)methyl tether at the C-2 position is described. The reaction starts with an acid-promoted semipinacol rearrangement to give a ring contraction cyclopentanone moiety bearing an arylpropargylaminoacetyl side chain. A subsequent alkyne-ketone metathesis affords the pyrrole derivatives in good yields. The 3,4-disubstituted furan analogues can also be available from 3,5,5-trimethyl-2,3-epoxycyclohexan-1-ones with a tethered arylpropargyl methyl ether at the C-2 position and BF₃·OEt₂ under an atmosphere of oxygen.

Original language	English
Pages (from-to)	12381-12396
Number of pages	16
Journal	Journal of Organic Chemistry
Volume	78
Issue number	24
DOIs	https://doi.org/10.1021/jo402025z
Publication status	Published - 2013 Dec 20

ASJC Scopus subject areas

Organic Chemistry

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CCDC 946900: Experimental Crystal Structure Determination
Yeh, M. P. (Creator), Lin, M. (Creator), Hsu, C. (Creator) & Liang, C. (Creator), Unknown Publisher, 2014
DOI: 10.5517/cc10sb59, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc10sb59&sid=DataCite
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CCDC 946898: Experimental Crystal Structure Determination
Yeh, M. P. (Creator), Lin, M. (Creator), Hsu, C. (Creator) & Liang, C. (Creator), Unknown Publisher, 2014
DOI: 10.5517/cc10sb37, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc10sb37&sid=DataCite
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CCDC 946905: Experimental Crystal Structure Determination
Yeh, M. P. (Creator), Lin, M. (Creator), Hsu, C. (Creator) & Liang, C. (Creator), Unknown Publisher, 2014
DOI: 10.5517/cc10sbbg, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc10sbbg&sid=DataCite
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Yeh, M. C. P., Lin, M. N., Hsu, C. H., & Liang, C. J. (2013). Syntheses of 3,4-disubstituted pyrroles and furans via Lewis acid-promoted semipinacol rearrangement/alkyne-ketone metathesis reaction of (C)-2- N - Or O-((3-arylpropargyl)methyl)-tethered 3,5,5-trimethyl-2,3-epoxycyclohexan-1-ones. Journal of Organic Chemistry, 78(24), 12381-12396. https://doi.org/10.1021/jo402025z

Syntheses of 3,4-disubstituted pyrroles and furans via Lewis acid-promoted semipinacol rearrangement/alkyne-ketone metathesis reaction of (C)-2- N - Or O-((3-arylpropargyl)methyl)-tethered 3,5,5-trimethyl-2,3-epoxycyclohexan-1-ones. / Yeh, Ming Chang P.; Lin, Ming Nan; Hsu, Ching Hsien et al.
In: Journal of Organic Chemistry, Vol. 78, No. 24, 20.12.2013, p. 12381-12396.

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

Yeh, MCP, Lin, MN, Hsu, CH & Liang, CJ 2013, 'Syntheses of 3,4-disubstituted pyrroles and furans via Lewis acid-promoted semipinacol rearrangement/alkyne-ketone metathesis reaction of (C)-2- N - Or O-((3-arylpropargyl)methyl)-tethered 3,5,5-trimethyl-2,3-epoxycyclohexan-1-ones', Journal of Organic Chemistry, vol. 78, no. 24, pp. 12381-12396. https://doi.org/10.1021/jo402025z

Yeh, Ming Chang P. ; Lin, Ming Nan ; Hsu, Ching Hsien et al. / Syntheses of 3,4-disubstituted pyrroles and furans via Lewis acid-promoted semipinacol rearrangement/alkyne-ketone metathesis reaction of (C)-2- N - Or O-((3-arylpropargyl)methyl)-tethered 3,5,5-trimethyl-2,3-epoxycyclohexan-1-ones. In: Journal of Organic Chemistry. 2013 ; Vol. 78, No. 24. pp. 12381-12396.

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abstract = "The synthesis of 2,3-disubstituted pyrroles via TMSOTf-assisted cyclization reaction of 3,5,5-trimethyl-2,3-epoxycyclohexan-1-ones incorporating a (3-arylpropargyltosylamino)methyl tether at the C-2 position is described. The reaction starts with an acid-promoted semipinacol rearrangement to give a ring contraction cyclopentanone moiety bearing an arylpropargylaminoacetyl side chain. A subsequent alkyne-ketone metathesis affords the pyrrole derivatives in good yields. The 3,4-disubstituted furan analogues can also be available from 3,5,5-trimethyl-2,3-epoxycyclohexan-1-ones with a tethered arylpropargyl methyl ether at the C-2 position and BF3·OEt2 under an atmosphere of oxygen.",

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Syntheses of 3,4-disubstituted pyrroles and furans via Lewis acid-promoted semipinacol rearrangement/alkyne-ketone metathesis reaction of (C)-2- N - Or O-((3-arylpropargyl)methyl)-tethered 3,5,5-trimethyl-2,3-epoxycyclohexan-1-ones

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CCDC 946900: Experimental Crystal Structure Determination

CCDC 946898: Experimental Crystal Structure Determination

CCDC 946905: Experimental Crystal Structure Determination

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