Asymmetric N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with α-Chloro Aldehydes

Xiaoxiao Song; Qijian Ni; Chen Zhu; Gerhard Raabe; Dieter Enders

doi:10.1055/s-0034-1379369

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(03): 421-428
DOI: 10.1055/s-0034-1379369

paper

Asymmetric N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with α-Chloro Aldehydes

Xiaoxiao Song

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Fax: +49(241)8092127 eMail: enders@rwth-aachen.de

,

Qijian Ni

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Fax: +49(241)8092127 eMail: enders@rwth-aachen.de

,

Chen Zhu

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Fax: +49(241)8092127 eMail: enders@rwth-aachen.de

,

Gerhard Raabe

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Fax: +49(241)8092127 eMail: enders@rwth-aachen.de

,

Dieter Enders*

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Fax: +49(241)8092127 eMail: enders@rwth-aachen.de

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Dedicated to Professor Martin Jansen on the occasion of his 70^th 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 - annulation

Volltext

Referenzen

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

For selected examples, see:

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

For selected reviews, see:

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

For a review, see:

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

25a Borg T, Danielsson J, Somfai P. Chem. Commun. 2010; 46: 1281
25b Halland N, Braunton A, Bachmann S, Marigo M, Jørgensen KA. J. Am. Chem. Soc. 2004; 126: 4790

Zusatzmaterial

Supporting Information