N-Heterocyclic Carbene Catalyzed Asymmetric Synthesis of Dihydropyranothiazoles­ via Azolium Enolate Intermediates

Abstract

A highly diastereo- and enantiostereoselective synthesis of bicyclic dihydropyranothiazoles combining a thiazole and δ-lactone skeleton via NHC-catalyzed [4+2] annulation of 5-alkenylthiazolones and α-chloroaldehydes has been developed. The heterocyclic products are formed via azolium enolate intermediates in good yields with high diastereo- and enantistereoselectivities.

Key words

asymmetric synthesis - dihydropyranone thiazole - N-heterocyclic carbene - organocatalysis - [4+2] annulation

• References

• 1a Breslow R. J. Am. Chem. Soc. 1958; 80: 3719
• 1b Sheehan JC. Hunneman DH. J. Am. Chem. Soc. 1966; 88: 3666
• 1c Enders D. Breuer K. Raabe G. Runsink J. Teles JH. Melder J.-P. Ebel K. Brode S. Angew. Chem., Int. Ed. Engl. 1995; 34: 1021
• 1d Enders D. Balensiefer T. Acc. Chem. Res. 2004; 37: 534
• 1e Enders D. Niemeier O. Henseler A. Chem. Rev. 2007; 107: 5606
• 1f Marion N. Díez-González S. Nolan SP. Angew. Chem. Int. Ed. 2007; 46: 298
• 1g Nair V. Vellalath S. Babu BP. Chem. Soc. Rev. 2008; 37: 2691
• 1h Benhamou L. Chardon E. Lavigne G. Bellemin-Laponnaz S. César V. Chem. Rev. 2011; 111: 2705
• 1i Flanigan DM. Romanov-Michailidis F. White NA. Rovis T. Chem. Rev. 2015; 115: 9307
• 2a Zeitler K. Angew. Chem. Int. Ed. 2005; 44: 7506
• 2b Huang X.-L. He L. Shao P.-L. Ye S. Angew. Chem. Int. Ed. 2009; 48: 192
• 2c Moore JL. Rovis T. Carbene Catalysts . In Asymmetric Organocatalysis . List B. Springer; Berlin: 2010: 78
• 2d Wu Y. Yao W. Pan L. Zhang Y. Ma C. Org. Lett. 2010; 12: 640
• 2e Jian T.-Y. He L. Tang C. Ye S. Angew. Chem. Int. Ed. 2011; 50: 9104
• 2f Nair V. Menon RS. Biju AT. Sinu CR. Paul RR. Jose A. Sreekumar V. Chem. Soc. Rev. 2011; 40: 5336
• 2g Bugaut X. Glorius F. Chem. Soc. Rev. 2012; 41: 3511
• 2h Douglas J. Churchill G. Smith AD. Synthesis 2012; 44: 2295
• 2i Grossmann A. Enders D. Angew. Chem. Int. Ed. 2012; 51: 314
• 2j Hao L. Du Y. Lv H. Chen X. Jiang H. Shao Y. Chi YR. Org. Lett. 2012; 14: 2154
• 2k Izquierdo J. Hutson GE. Cohen DT. Scheidt KA. Angew. Chem. Int. Ed. 2012; 51: 11686
• 2l Chen X.-Y. Sun L.-H. Ye S. Chem. Eur. J. 2013; 19: 4441
• 2m De Sarkar S. Biswas A. Samanta RC. Studer A. Chem. Eur. J. 2013; 19: 4664
• 2n Ryan SJ. Candish L. Lupton DW. Chem. Soc. Rev. 2013; 42: 4906
• 2o Hopkinson MN. Richter C. Schedler M. Glorius F. Nature 2014; 510: 485
• 2p Mahatthananchai J. Bode JW. Acc. Chem. Res. 2014; 47: 696
• 2q Lee A. Scheidt KA. Chem. Commun. 2015; 51: 3407
• 2r Menon RS. Biju AT. Nair V. Chem. Soc. Rev. 2015; 44: 5040
• 2s Yetra SR. Patra A. Biju AT. Synthesis 2015; 47, 1357
• 2t Wang L. Li S. Blümel M. Philipps AR. Wang A. Puttreddy R. Rissanen K. Enders D. Angew. Chem. Int. Ed. 2016; 55: 11110
• 2u Reyes E. Uria U. Carrillo L. Vicario JL. Synthesis 2017; 49: 451
• 2v Wang L. Li S. Blümel M. Puttreddy R. Peuronen A. Rissanen K. Enders D. Angew. Chem. Int. Ed. 2017; 56: 8516
• 3a Vora HU. Rovis T. Aldrichimica Acta 2011; 44: 3
• 3b Vora HU. Wheeler P. Rovis T. Adv. Synth. Catal. 2012; 354: 1617
• 3c Fraile A. Parra A. Tortosa M. Alemán J. Tetrahedron 2014; 70: 9145
• 4 Reynolds NT. Read de Alaniz J. Rovis T. J. Am. Chem. Soc. 2004; 126: 9518
• 5a He M. Uc GJ. Bode JW. J. Am. Chem. Soc. 2006; 128: 15088
• 5b Bode JW. Sohn SS. J. Am. Chem. Soc. 2007; 129: 13798
• 5c Rong Z.-Q. Jia M.-Q. You S.-L. Tetrahedron 2011; 67: 9329
• 5d Yang L. Wang F. Chua PJ. Lv Y. Zhong L.-J. Zhong G. Org. Lett. 2012; 14: 2894
• 5e Zhang H.-M. Lv H. Ye S. Org. Biomol. Chem. 2013; 11: 6255
• 5f Yang L. Wang F. Lee R. Lv Y. Huang K.-W. Zhong G. Org. Lett. 2014; 16: 3872
• 5g Ni Q. Song X. Xiong J. Raabe G. Enders D. Chem. Commun. 2015; 51: 1263
• 5h Gao Z.-H. Chen X.-Y. Cheng J.-T. Liao W.-L. Ye S. Chem. Commun. 2015; 51: 9328
• 5i Lin L. Yang Y. Wang M. Lai L. Guo Y. Wang R. Chem. Commun. 2015; 51: 8134
• 6 Luzina EL. Popov AV. Eur. J. Med. Chem. 2009; 44: 4944
• 7 Zaharia V. Ignat A. Palibroda N. Ngameni B. Kuete V. Fokunang CN. Moungang ML. Ngadjui BT. Eur. J. Med. Chem. 2010; 45: 5080
• 8 Bartolomé-Nebreda JM. Conde-Ceide S. Delgado F. Iturrino L. Pastor J. Pena M. Á. Trabanco AA. Tresadern G. Wassvik CM. Stauffer SR. Jadhav S. Gogi K. Vinson PN. Noetzel MJ. Days E. Weaver CD. Lindsley CW. Niswender CM. Jones CK. Conn PJ. Rombouts F. Lavreysen H. Macdonald GJ. Mackie C. Steckler T. J. Med. Chem. 2013; 56: 7243
• 9a John TF. French LG. Erlichman JS. Eur. J. Pharmacol. 2006; 545: 129
• 9b McCurdy CR. Sufka KJ. Smith GH. Warnick JE. Nieto MJ. Pharmacol. Biochem. Behav. 2006; 83: 109
• 9c Prisinzano TE. J. Nat. Prod. 2008; 72: 581
• 10 Li S. Chen X.-Y. Liu Q. von Essen C. Rissanen K. Enders D. Synthesis 2017; 49: 4861
• 11 CCDC 1587163 (3d) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
• 12a Kerr MS. Read de Alaniz J. Rovis T. J. Org. Chem. 2005; 70: 5725
• 12b He M. Struble JR. Bode JW. J. Am. Chem. Soc. 2006; 128: 8418
• 13a Mowat J. Gries R. Khaskin G. Gries G. Britton R. J. Nat. Prod. 2009; 72: 772
• 13b Bai H.-W. Cai Z.-J. Wang S.-Y. Ji S.-J. Org. Lett. 2015; 17: 2898