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Synthesis 2012; 44(23): 3579-3589
DOI: 10.1055/s-0032-1317495
DOI: 10.1055/s-0032-1317495
feature article
Diastereoselective Synthesis of Substituted Tetrahydropyrans by Copper(II)–Bisphosphine-Catalyzed Olefin Migration and Prins Cyclization
Further Information
Publication History
Received: 06 July 2012
Accepted after revision: 30 September 2012
Publication Date:
06 November 2012 (online)
Abstract
We developed a copper(II) triflate–bisphosphine complex catalyzed olefin migration and Prins cyclization which lead to the synthesis of substituted tetrahydropyran derivatives. The protocol is convenient and a variety of substituted tetrahydropyrans were obtained in good to excellent yields with excellent diastereoselectivities.
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References
- 1a Reymond S, Ferrie L, Guerinot A, Capdevielle P, Cossy J. Pure Appl. Chem. 2008; 80: 1683
- 1b Sanz MA, Voigt T, Waldmann H. Adv. Synth. Catal. 2006; 348: 1511
- 1c Elliott MC. J. Chem. Soc., Perkin Trans. 1 2002; 2301
- 1d Nakata T. Chem. Rev. 2005; 105: 4314
- 1e Gademann K, Portmann C. Curr. Org. Chem. 2008; 12: 326
- 2a Carrillo R, Leon LG, Martın T, Martın VS, Padron JM. Bioorg. Med. Chem. Lett. 2006; 16: 6135
- 2b Singh P, Bhardwaj A. J. Med. Chem. 2010; 53: 3707
- 2c Ghosh AK, Bilcer G, Schiltz G. Synthesis 2001; 2203
- 2d List B, Castello C. Synlett 2001; 1687
- 3a Ghosh AK, Anderson DD. Future Med. Chem. 2011; 3: 1181
- 3b Wender PA, Baryza JL, Brenner SE, Clarke MO, Gamber CG, Horan JC, Jessop TC, Kan C, Pattabiraman K, Williams TJ. Pure Appl. Chem. 2003; 75: 143
- 4a Ghosh AK, Chapsal BD, Baldridge A, Steffey MP, Walters DE, Koh Y, Amano M, Mitsuya H. J. Med. Chem. 2011; 54: 622
- 4b Ide K, Aoki M, Amano M, Koh Y, Yedidi RS, Das D, Leschenko S, Chapsal B, Ghosh AK, Mitsuya H. Antimicrob. Agents Chemother. 2011; 55: 1717
- 5 Tietze LF, Kettschau G, Gewer JA, Schuffenhauer A. Curr. Org. Chem. 1998; 2: 19
- 6 Pellissier H. Tetrahedron 2009; 65: 2839
- 7 Yadav JS, Purnima KV, Reddy BV. S, Nagaih K, Ghamdi AK. Tetrahedron Lett. 2011; 52: 6709
- 8 Nising CF, Brase S. Chem. Soc. Rev. 2008; 1218
- 9 Smith III AB, Fox RJ, Razler TM. Acc. Chem. Res. 2008; 41: 675
- 10 Clarke PA, Martin WH. C, Hargreaves JM, Wilson C, Blake AJ. Org. Biomol. Chem. 2005; 3: 3551
- 11a Ghosh AK, Nicponski DR. Org. Lett. 2011; 13: 4328
- 11b Ghosh AK, Nicponski DR, Kass J. Tetrahedron Lett. 2012; 53: 3699
- 12 Miura K, Horiike M, Inoue G, Ichikawa J, Hosomi A. Chem. Lett. 2008; 37: 270
- 13 Loh T.-P, Hu Q.-Y, Tan K.-T, Cheng H.-S. Org. Lett. 2001; 3: 2669
- 14 For examples of Lewis acid catalyzed ene reactions, see: Snider BB, Rodini DJ, Kirk TC, Cordova R. J. Am. Chem. Soc. 1982; 104: 555
-
15 Qian H, Han X, Widenhoefer RA. J. Am. Chem. Soc. 2004; 126: 9536
-
16 Clarke ML, France MB. Tetrahedron 2008; 64: 9003
-
17 Tolman CA. Chem. Rev. 1977; 77: 313
- 18 Zimmerman HE, Traxler MD. J. Am. Chem. Soc. 1957; 79: 1920
- 19 Mikami K, Shimizu M. Chem. Rev. 1992; 92: 1021
- 20 Kocovsky P, Ahmed G, Srogl J, Malkov AV, Steele J. J. Org. Chem. 1999; 64: 2765
- 21 Gesinski MR, Van Orden LJ, Rychnovsky SD. Synlett 2008; 363
-
22 Tadpetch K, Rychnovsky SD. Org. Lett. 2008; 10: 4839
- 23 Cloninger MJ, Overman LE. J. Am. Chem. Soc. 1999; 121: 1092
- 24 Inoue S, Asami M, Honda K, Miyazaki H. Chem. Lett. 1996; 10: 889
- 25 Rychnovski SD, Jasti R. J. Am. Chem. Soc. 2006; 128: 13640
- 26 Corey EJ, Bakshi RK, Shibata S. J. Am. Chem. Soc. 1987; 109: 5551