Enamide-benzyne-[2 + 2] cycloaddition: stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions

doi:10.1021/ol901434g

. 2009 Aug 20;11(16):3666-9.

doi: 10.1021/ol901434g.

Enamide-benzyne-[2 + 2] cycloaddition: stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions

John B Feltenberger¹, Ryuji Hayashi, Yu Tang, Eric S C Babiash, Richard P Hsung

Affiliations

PMID: 19624104
PMCID: PMC2822464
DOI: 10.1021/ol901434g

Enamide-benzyne-[2 + 2] cycloaddition: stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions

John B Feltenberger et al. Org Lett. 2009.

. 2009 Aug 20;11(16):3666-9.

doi: 10.1021/ol901434g.

Authors

John B Feltenberger¹, Ryuji Hayashi, Yu Tang, Eric S C Babiash, Richard P Hsung

Affiliation

¹ Department of Chemistry and Division of Pharmaceutical Sciences, University of Wisconsin, Madison, Wisconsin 53705, USA.

PMID: 19624104
PMCID: PMC2822464
DOI: 10.1021/ol901434g

Abstract

Benzyne-[2 + 2] cycloadditions with enamides are described. This effort led to the development of a highly stereoselective tandem [2 + 2] cycloaddition-pericyclic ring-opening-intramolecular-N-tethered-[4 + 2] cycloaddition for rapid assembly of nitrogen heterocycles.

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Figures

**Scheme 1**
A Tandem Benzyne-Enamide-[2 + 2]–Diels-Alder.

**Scheme 2**
A Tandem Benzyne-Enamide-[2 + 2]–[4 + 2].

**Scheme 3**
Substituted Olefins for [4 + 2] Cycloaddition.

**Scheme 4**
An Asymmetric Tandem [2 + 2]–[4 + 2].

See this image and copyright information in PMC

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References

1. For recent reviews on the aryne chemistry, see:
2. Peña D, Pérez D, Guitián E. Angew Chem Int Ed. 2006;45:3579. - PubMed
3. Pellissier H, Santelli M. Tetrahedron. 2003;59:701.
4. Kessar SV. In: Comprehensive Organic Synthesis. Trost BM, Fleming I, editors. Vol. 4. Pergamon Press; New York: 1991. pp. 483–515.
5. Heaney H. Chem Rev. 1962;62:81.
1. For leading examples of nucleophilic additions, see:
2. Liu Z, Larock RC. Org Lett. 2004;6:99. - PubMed
3. Jeganmohn M, Chen CH. Org Lett. 2004;6:2821. - PubMed
4. Jeganmohan M, Cheng CH. Synthesis. 2005:1693.
5. Bhuvaneswari S, Jeganmohan M, Yang MC, Cheng CH. Chem Commun. 2008:2158. - PubMed
6. Xie C, Liu L, Zhang Y, Xu P. Org Lett. 2008;10:2393. - PubMed
7. Sha F, Huang X. Angew Chem Int Ed. 2009;38:3458. - PubMed
1. For examples of interesting insertion type processes, see:
2. Liu Z, Larock RC. J Am Chem Soc. 2005;127:13112. - PubMed
3. Tambar UK, Stoltz BM. J Am Chem Soc. 2005;127:5340. - PubMed
4. Tambar UK, Ebner DC, Stoltz BM. J Am Chem Soc. 2006;127:11752. - PMC - PubMed
5. Pi SF, Tang BX, Li JH, Liu YL, Liang Y. Org Lett. 2009;11:2309. - PubMed
6. Also see reference 1a
7. None
1. For recent examples on annulations and cycloadditions, see:
2. Liu Z, Larock RC. Tetrahedron. 2007;63:347. - PMC - PubMed
3. Liu Z, Shi F, Martinez PDG, Raminelli C, Larock RC. J Org Chem. 2008;73:219. - PubMed
4. Shi F, Waldo JP, Chen Y, Larock RC. Org Lett. 2008;10:2409. - PMC - PubMed
5. Worlikar SA, Larock RC. Org Lett. 2009;11:2413. - PMC - PubMed
6. Also see reference 6
7. None
1. For a mild and general preparation of arynes using ortho-(trimethylsilyl)aryl triflates, see:
2. Himeshima Y, Sonoda T, Kobayashi H. Chem Lett. 1983:1211.

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[1] For recent reviews on the aryne chemistry, see:

Peña D, Pérez D, Guitián E. Angew Chem Int Ed. 2006;45:3579. - PubMed

Pellissier H, Santelli M. Tetrahedron. 2003;59:701.

Kessar SV. In: Comprehensive Organic Synthesis. Trost BM, Fleming I, editors. Vol. 4. Pergamon Press; New York: 1991. pp. 483–515.

Heaney H. Chem Rev. 1962;62:81.

[2] For recent reviews on the aryne chemistry, see:

[3] Peña D, Pérez D, Guitián E. Angew Chem Int Ed. 2006;45:3579. - PubMed

[4] Pellissier H, Santelli M. Tetrahedron. 2003;59:701.

[5] Kessar SV. In: Comprehensive Organic Synthesis. Trost BM, Fleming I, editors. Vol. 4. Pergamon Press; New York: 1991. pp. 483–515.

[6] Heaney H. Chem Rev. 1962;62:81.

[7] For leading examples of nucleophilic additions, see:

Liu Z, Larock RC. Org Lett. 2004;6:99. - PubMed

Jeganmohn M, Chen CH. Org Lett. 2004;6:2821. - PubMed

Jeganmohan M, Cheng CH. Synthesis. 2005:1693.

Bhuvaneswari S, Jeganmohan M, Yang MC, Cheng CH. Chem Commun. 2008:2158. - PubMed

Xie C, Liu L, Zhang Y, Xu P. Org Lett. 2008;10:2393. - PubMed

Sha F, Huang X. Angew Chem Int Ed. 2009;38:3458. - PubMed

[8] For leading examples of nucleophilic additions, see:

[9] Liu Z, Larock RC. Org Lett. 2004;6:99. - PubMed

[10] Jeganmohn M, Chen CH. Org Lett. 2004;6:2821. - PubMed

[11] Jeganmohan M, Cheng CH. Synthesis. 2005:1693.

[12] Bhuvaneswari S, Jeganmohan M, Yang MC, Cheng CH. Chem Commun. 2008:2158. - PubMed

[13] Xie C, Liu L, Zhang Y, Xu P. Org Lett. 2008;10:2393. - PubMed

[14] Sha F, Huang X. Angew Chem Int Ed. 2009;38:3458. - PubMed

[15] For examples of interesting insertion type processes, see:

Liu Z, Larock RC. J Am Chem Soc. 2005;127:13112. - PubMed

Tambar UK, Stoltz BM. J Am Chem Soc. 2005;127:5340. - PubMed

Tambar UK, Ebner DC, Stoltz BM. J Am Chem Soc. 2006;127:11752. - PMC - PubMed

Pi SF, Tang BX, Li JH, Liu YL, Liang Y. Org Lett. 2009;11:2309. - PubMed

Also see reference 1a

None

[16] For examples of interesting insertion type processes, see:

[17] Liu Z, Larock RC. J Am Chem Soc. 2005;127:13112. - PubMed

[18] Tambar UK, Stoltz BM. J Am Chem Soc. 2005;127:5340. - PubMed

[19] Tambar UK, Ebner DC, Stoltz BM. J Am Chem Soc. 2006;127:11752. - PMC - PubMed

[20] Pi SF, Tang BX, Li JH, Liu YL, Liang Y. Org Lett. 2009;11:2309. - PubMed

[21] Also see reference 1a

[22] None

[23] For recent examples on annulations and cycloadditions, see:

Liu Z, Larock RC. Tetrahedron. 2007;63:347. - PMC - PubMed

Liu Z, Shi F, Martinez PDG, Raminelli C, Larock RC. J Org Chem. 2008;73:219. - PubMed

Shi F, Waldo JP, Chen Y, Larock RC. Org Lett. 2008;10:2409. - PMC - PubMed

Worlikar SA, Larock RC. Org Lett. 2009;11:2413. - PMC - PubMed

Also see reference 6

None

[24] For recent examples on annulations and cycloadditions, see:

[25] Liu Z, Larock RC. Tetrahedron. 2007;63:347. - PMC - PubMed

[26] Liu Z, Shi F, Martinez PDG, Raminelli C, Larock RC. J Org Chem. 2008;73:219. - PubMed

[27] Shi F, Waldo JP, Chen Y, Larock RC. Org Lett. 2008;10:2409. - PMC - PubMed

[28] Worlikar SA, Larock RC. Org Lett. 2009;11:2413. - PMC - PubMed

[29] Also see reference 6

[30] None

[31] For a mild and general preparation of arynes using ortho-(trimethylsilyl)aryl triflates, see:

Himeshima Y, Sonoda T, Kobayashi H. Chem Lett. 1983:1211.

[32] For a mild and general preparation of arynes using ortho-(trimethylsilyl)aryl triflates, see:

[33] Himeshima Y, Sonoda T, Kobayashi H. Chem Lett. 1983:1211.

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Enamide-benzyne-[2 + 2] cycloaddition: stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions

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Enamide-benzyne-[2 + 2] cycloaddition: stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions

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