RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2015; 47(03): 421-428
DOI: 10.1055/s-0034-1379369
DOI: 10.1055/s-0034-1379369
paper
Asymmetric N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with α-Chloro Aldehydes
Weitere Informationen
Publikationsverlauf
Received: 26. September 2014
Accepted after revision: 30. September 2014
Publikationsdatum:
06. November 2014 (online)
Dedicated to Professor Martin Jansen on the occasion of his 70th birthday
Abstract
Diastereo- and enantioselective N-heterocyclic carbene catalyzed 1-azadiene Diels–Alder reactions of (E)-2-styrylbenzothiazoles with α-chloro aldehydes are reported. This annulation strategy provides an efficient access to medicinally important dihydrobenzothiazolopyridin-1-ones in good to excellent yields (44–97%) with very good to excellent stereoselectivities (up to 9:1 dr, 98% ee) and tolerates quite a range of substituents.
Key words
N-heterocyclic carbenes - organocatalysis - asymmetric synthesis - aza-Diels–Alder reaction - annulationSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379369. Included are copies of the 1H and 13C NMR spectra of products 3a–l, HPLC measurements of products 3a–l, and the NOESY spectrum of 3d.
- Supporting Information
-
References
- 1a Girling PR, Kiyoi T, Whiting A. Org. Biomol. Chem. 2011; 9: 3105
- 1b Masson G, Lalli C, Benohoud M, Dagousset G. Chem. Soc. Rev. 2013; 42: 902
- 2 Serckx-Poncin B, Hesbain-Frisque A.-M, Ghosez L. Tetrahedron Lett. 1982; 23: 3261
- 3a Danishefsky S, Kerwin JF. Jr. J. Org. Chem. 1982; 47: 3183
- 3b Kerwin JF. Jr, Danishefsky S. Tetrahedron Lett. 1982; 23: 3739
- 4a Shang D, Xin J, Liu Y, Zhou X, Liu X, Feng X. J. Org. Chem. 2008; 73: 630
- 4b Sridharan V, Perumal PT, Avendaño C, Menéndez JC. Org. Biomol. Chem. 2007; 5: 1351
- 4c Xie M, Chen X, Zhu Y, Gao B, Lin L, Liu X, Feng X. Angew. Chem. Int. Ed. 2010; 49: 3799
- 4d Wakabayashi R, Kurahashi T, Matsubara S. Org. Lett. 2012; 14: 4794
- 4e Deng Y, Liu L, Sarkisian RG, Wheeler K, Wang H, Xu Z. Angew. Chem. Int. Ed. 2013; 52: 3663
- 4f Eschenbrenner-Lux V, Küchler P, Ziegler S, Kumar K, Waldmann H. Angew. Chem. Int. Ed. 2014; 53: 2134
- 5a Itoh T, Yokoya M, Miyauchi K, Nagata K, Ohsawa A. Org. Lett. 2003; 5: 4301
- 5b Itoh T, Yokoya M, Miyauchi K, Nagata K, Ohsawa A. Org. Lett. 2006; 8: 1533
- 5c Han B, Li J.-L, Ma C, Zhang S.-J, Chen Y.-C. Angew. Chem. Int. Ed. 2008; 47: 9971
- 5d Han B, He Z.-Q, Li J.-L, Li R, Jiang K, Liu T.-Y, Chen Y.-C. Angew. Chem. Int. Ed. 2009; 48: 5474
- 5e Li J.-L, Zhou S.-L, Han B, Wu L, Chen Y.-C. Chem. Commun. 2010; 46: 2665
- 5f Zhou S.-L, Li J.-L, Dong L, Chen Y.-C. Org. Lett. 2011; 13: 5874
- 5g Gu J, Ma C, Li Q.-Z, Du W, Chen Y.-C. Org. Lett. 2014; 16: 3986
- 6 Lalonde MP, McGowan MA, Rajapaksa NS, Jacobsen EN. J. Am. Chem. Soc. 2013; 135: 1891
- 7a Itoh J, Fuchibe K, Akiyama T. Angew. Chem. Int. Ed. 2006; 45: 4796
- 7b Akiyama T, Morita H, Fuchibe K. J. Am. Chem. Soc. 2006; 128: 13070
- 7c He L, Bekkaye M, Retailleau P, Masson G. Org. Lett. 2012; 14: 3158
- 7d He L, Laurent G, Retailleau P, Folléas B, Brayer J.-L, Masson G. Angew. Chem. Int. Ed. 2013; 52: 11088
- 7e Brioche J, Courant T, Alcaraz L, Stocks M, Furber M, Zhu J, Masson G. Adv. Synth. Catal. 2014; 356: 1719
- 8a Enders D, Balensiefer T. Acc. Chem. Res. 2004; 37: 534
- 8b Enders D, Niemeier O, Henseler A. Chem. Rev. 2007; 107: 5606
- 8c Biju AT, Kuhl N, Glorius F. Acc. Chem. Res. 2011; 44: 1182
- 8d Izquierdo J, Hutson GE, Cohen DT, Scheidt KA. Angew. Chem. Int. Ed. 2012; 51: 11686
- 8e Grossmann A, Enders D. Angew. Chem. Int. Ed. 2012; 51: 314
- 8f Bugaut X, Glorius F. Chem. Soc. Rev. 2012; 41: 3511
- 8g Ryan SJ, Candish L, Lupton DW. Chem. Soc. Rev. 2013; 42: 4906
- 8h De Sarkar S, Biswas A, Samanta RC, Studer A. Chem. Eur. J. 2013; 19: 4664
- 8i Mahatthananchai J, Bode JW. Acc. Chem. Res. 2014; 47: 696
- 8j Hopkinson MN, Richter C, Schedler M, Glorius F. Nature 2014; 510: 485
- 8k Abbasov ME, Romo D. Nat. Prod. Rep. 2014; 31: 1318
- 9a Burstein C, Glorius F. Angew. Chem. Int. Ed. 2004; 43: 6205
- 9b Sohn SS, Rosen EL, Bode JW. J. Am. Chem. Soc. 2004; 126: 14370
- 9c Nair V, Menon RS, Biju AT, Sinu CR, Paul RR, Jose A, Sreekumar V. Chem. Soc. Rev. 2011; 40: 5336
- 10a Reynolds NT, Rovis T. J. Am. Chem. Soc. 2005; 127: 16406
- 10b Douglas J, Churchill G, Smith AD. Synthesis 2012; 44: 2295
- 10c Vora HU, Wheeler P, Rovis T. Adv. Synth. Catal. 2012; 354: 1617
- 11a Zhang Y.-R, He L, Wu X, Shao P.-L, Ye S. Org. Lett. 2008; 10: 277
- 11b Duguet N, Campbell CD, Slawin AM. Z, Smith AD. Org. Biomol. Chem. 2008; 6: 1108
- 11c He L, Lv H, Zhang Y.-R, Ye S. J. Org. Chem. 2008; 73: 8101
- 11d Wang X.-N, Shao P.-L, Lv H, Ye S. Org. Lett. 2009; 11: 4029
- 11e Huang X.-L, Chen X.-Y, Ye S. J. Org. Chem. 2009; 74: 7585
- 11f Wang X.-N, Zhang Y.-Y, Ye S. Adv. Synth. Catal. 2010; 352: 1892
- 11g Wang T, Huang X.-L, Ye S. Org. Biomol. Chem. 2010; 8: 5007
- 11h Jian T.-Y, He L, Tang C, Ye S. Angew. Chem. Int. Ed. 2011; 50: 9104
- 11i Zhang H.-M, Gao Z.-H, Ye S. Org. Lett. 2014; 16: 3079
- 12a Shao P.-L, Chen X.-Y, Ye S. Angew. Chem. Int. Ed. 2010; 49: 8412
- 12b Li L, Du D, Ren J, Wang Z. Eur. J. Org. Chem. 2011; 614
- 12c Ni Q, Zhang H, Grossmann A, Loh CC. J, Merkens C, Enders D. Angew. Chem. Int. Ed. 2013; 52: 13562
- 13a He M, Uc GJ, Bode JW. J. Am. Chem. Soc. 2006; 128: 15088
- 13b Zhang Y.-R, Lv H, Zhou D, Ye S. Chem. Eur. J. 2008; 14: 8473
- 13c Huang X.-L, He L, Shao P.-L, Ye S. Angew. Chem. Int. Ed. 2009; 48: 192
- 13d Kaeobamrung J, Kozlowski MC, Bode JW. Proc. Natl. Acad. Sci. U.S.A. 2010; 107: 20661
- 13e Lv H, Chen X.-Y, Sun L.-H, Ye S. J. Org. Chem. 2010; 75: 6973
- 13f Fang X, Chen X, Chi YR. Org. Lett. 2011; 13: 4708
- 13g Lv H, Mo J, Fang X, Chi YR. Org. Lett. 2011; 13: 5366
- 13h Yang L, Wang F, Chua PJ, Lv Y, Zhong L.-J, Zhong G. Org. Lett. 2012; 14: 2894
- 13i Allen SE, Mahatthananchai J, Bode JW, Kozlowski MC. J. Am. Chem. Soc. 2012; 134: 12098
- 13j Yang L, Wang F, Lee R, Lv Y, Huang K.-W, Zhong G. Org. Lett. 2014; 16: 3872
- 14 He M, Struble JR, Bode JW. J. Am. Chem. Soc. 2006; 128: 8418
- 15 Jian T.-Y, Shao P.-L, Ye S. Chem. Commun. 2011; 47: 2381
- 16 Jian T.-Y, Sun L.-H, Ye S. Chem. Commun. 2012; 48: 10907
- 17 Zhao X, Ruhl KE, Rovis T. Angew. Chem. Int. Ed. 2012; 51: 12330
- 18a Hao L, Du Y, Lv H, Chen X, Jiang H, Shao Y, Chi YR. Org. Lett. 2012; 14: 2154
- 18b Hao L, Chuen CW, Ganguly R, Chi YR. Synlett 2013; 24: 1197
- 19 Haddach M, Schwaebe MK, Michaux J, Nagasawa J, O’Brien SE, Whitten JP, Pierre F, Kerdoncuff P, Darjania L, Stansfield R, Drygin D, Anderes K, Proffitt C, Bliesath J, Siddiqui-Jain A, Omori M, Huser N, Rice WG, Ryckman DM. ACS Med. Chem. Lett. 2012; 3: 602
- 20 Dinakaran M, Senthilkumar P, Yogeeswari P, China A, Nagaraja V, Sriram D. Bioorg. Med. Chem. 2008; 16: 3408
- 21 CCDC 1016815 contains the supplementary crystallographic data for compound 3d reported in this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
- 22 Leach AG, Houk KN. J. Org. Chem. 2001; 66: 5192
- 23a Thomson JE, Campbell CD, Concellon C, Duguet N, Rix K, Slawin AM. Z, Smith AD. J. Org. Chem. 2008; 73: 2784
- 23b Vora HU, Lathrop SP, Reynolds NT, Kerr MS, Read de Alaniz J, Rovis T. Org. Synth. 2010; 87: 350
- 23c Struble JR, Bode JW. Org. Synth. 2010; 87: 362
- 23d Ling KB, Smith AD. Chem. Commun. 2011; 47: 373
- 23e Campbell CD, Concellón C, Smith AD. Tetrahedron: Asymmetry 2011; 22: 797
- 24a Saito K, Kambe S, Nakano Y. Synthesis 1983; 210
- 24b Fathy NM, Abdel Motti FM, Elgemeie GE. H. Arch. Pharm. (Weinheim, Ger.) 1988; 321: 509
For selected examples, see:
For selected reviews, see:
For a review, see: