Synthesis 2017; 49(23): 5197-5202
DOI: 10.1055/s-0036-1588521
paper
© Georg Thieme Verlag Stuttgart · New York

Desymmetrization of Hepta-1,6-dien-4-ol by a Highly Stereo­selective Tandem Prins–Ritter Cyclization: Access to New THP Acetamides

Thomas Glachet, Fabienne Fache, Béatrice Pelotier, Olivier Piva*
  • Univ Lyon, Université Claude Bernard Lyon 1, CNRS, INSA Lyon, CPE Lyon, ICBMS, UMR 5246, 69622 Villeurbanne Cedex, France   Email: olivier.piva@univ-lyon1.fr
Further Information

Publication History

Received: 10 May 2017

Accepted after revision: 05 July 2017

Publication Date:
14 August 2017 (eFirst)

Abstract

Prins–Ritter cyclization performed from hepta-1,6-dien-4-ol and various aldehydes, promoted by bismuth(II) triflate, afforded N-(tetrahydropyranyl)acetamides in moderate to high yields. Subsequent Wacker-type oxidation using Dess–Martin periodinane (DMP) delivered the corresponding ketones.

Supporting Information

 
  • References

    • 1a Clarke PA. Santos S. Eur. J. Org. Chem. 2006; 2045
    • 1b Larrosa I. Romea P. Urpi F. Tetrahedron 2008; 64: 2683
    • 2a Nasir NM. Ermanis K. Clarke PA. Org. Biomol. Chem. 2014; 12: 3323
    • 2b Heravi MM. Ahmadi T. Ghavidel M. Heidari B. Hamidi H. RSC Adv. 2015; 5: 101999
    • 4a Ermanis K. Hsiao Y.-T. Kaya U. Jeuken A. Clarke PA. Chem. Sci. 2017; 8: 482
    • 4b Nicolaou KC. Rhoades D. Lamani M. Pattanayak MR. Kumar SM. J. Am. Chem. Soc. 2016; 138: 7532
    • 4c Athe S. Ghosh S. Synthesis 2016; 48: 917
    • 4d Srilatha M. Das B. Helv. Chim. Acta 2015; 98: 267
    • 4e Bates RW. Li L. Palani K. Phetsang W. Loh JK. Asian J. Org. Chem. 2014; 3: 792
    • 4f Gharpure SJ. Prasad JV. K. Bera K. Eur. J. Org. Chem. 2014; 3570
    • 4g Dai Q. Rana NK. Zhao JC.-G. Org. Lett. 2013; 15: 2922
    • 4h Wang L. Menche D. J. Org. Chem. 2012; 77: 10811
    • 4i Tomas L. Boije af Gennas G. Hiebel M.-A. Hampson P. Gueyrard D. Pelotier B. Yli-Kauhaluoma Y. Piva O. Lord JM. Goekjian PG. Chem. Eur. J. 2012; 18: 7452
    • 5a Greco SJ. Fiorot RG. Lacerda V. Dos Santos RB. Aldrichimica Acta 2013; 46: 59
    • 5b Pastor IM. Yus M. Curr. Org. Chem. 2012; 16: 1277
    • 5c Olier C. Kaafarani M. Gastaldi S. Bertrand MP. Tetrahedron 2010; 66: 413
    • 5d Subba Reddy BV. Borkar P. Yadav JS. Purushotham Reddy P. Kunwar AC. Sridhar C. Grée R. Org. Biomol. Chem. 2012; 10: 1349
    • 5e Chalopin T. Jebali K. Gaulon-Nourry C. Dénès F. Lebreton J. Mathé-Allainmat M. Tetrahedron 2016; 72: 318
    • 5f Beattie RJ. Hornsby TW. Craig G. Galan MC. Willis CL. Chem. Sci. 2016; 7: 2743
    • 5g Alvarez-Mendez SJ. Garcia C. Martin VS. Chem. Commun. 2016; 52: 3380
    • 6a Hiebel M.-A. Pelotier B. Piva O. Tetrahedron 2007; 63: 7874
    • 6b Clarisse D. Fache F. Tetrahedron Lett. 2014; 55: 2221
  • 7 Yin J. Kouda K. Tezuka Y. Tran QL. Miyahara T. Chen Y. Kadota S. Planta Med. 2004; 70: 54

    • For recent syntheses of diospongin A and stereomers:
    • 8a Nagarjuna B. Suresh N. Basaveswara Rao MV. Venkata Rao C. Pharma Chem. 2016; 8: 134
    • 8b Li Z. Tong R. Synthesis 2016; 48: 1630
    • 8c Gharpure SJ. Mane SP. Nanda LN. Shukla MK. Isr. J. Chem. 2016; 56: 553
    • 8d Zúñiga A. Pérez M. Gándara Z. Fall A. Gómez G. Fall Y. ARKIVOC 2015; (vii): 195
    • 8e Rybak T. Hall DG. Org. Lett. 2015; 17: 4156
    • 8f Merad J. Borkar P. Bouyon YT. Roux C. Pons J.-M. Parrain J.-L. Chuzel O. Bressy C. Org. Lett. 2015; 17: 2118
    • 8g Meruva SB. Mekala R. Raghunadh A. Rao KR. Dahanukar VH. Pratap TV. Syam Kumar UK. Dubey PK. Tetrahedron Lett. 2014; 55: 4739
    • 8h Stefan E. Nalin AP. Taylor RE. Tetrahedron 2013; 69: 7706
  • 9 Raffier L. Izquierdo F. Piva O. Synthesis 2011; 4037
  • 10 Ponra S. Majumdar KC. RSC Adv. 2016; 6: 37784
  • 11 Michel BW. Steffens LD. Sigman MS. Org. React. 2014; 84: 75-413

    • For a recent review on Ritter reactions, see:
    • 12a Guérinot A. Reymond S. Cossy J. Eur. J. Org. Chem. 2012; 19
    • 12b Jiang D. He T. Ma L. Wang Z. RSC Adv. 2014; 4: 64936
    • 13a Yadav JS. Subba Reddy BV. Aravind S. Narayana Kumar GG. K. S. Madhavi C. Kunwar AC. Tetrahedron 2008; 64: 3025
    • 13b Yadav JS. Reddy YJ. Reddy PA. N. Reddy BV. S. Org. Lett. 2013; 15: 546
    • 14a Srinivasan P. Perumal PT. Raja S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2011; 50: 1083
    • 14b Sabitha G. Bhikshapathi M. Nayak S. Yadav JS. Synth. Commun. 2011; 41: 8
  • 15 Reddy UC. Rama Raju B. Pramod Kumar EK. Saikia AK. J. Org. Chem. 2008; 73: 1628
    • 16a Yadav JS. Subba Reddy BV. Narayana Kumar GG. K. S. Madhusudhan Reddy G. Tetrahedron Lett. 2007; 48: 4903
    • 16b Selvam NP. Perumal PT. Can. J. Chem. 2009; 87: 698
  • 17 For a recent review on Bi(OTf)3, see: Ondet P. Lemière G. Dunach E. Eur. J. Org. Chem. 2017; 761
    • 19a Jasti R. Vitale J. Rychnovsky SD. J. Am. Chem. Soc. 2004; 126: 9904
    • 19b Clarisse D. Pelotier B. Piva O. Fache F. Chem. Commun. 2012; 48: 157
    • 19c Lolkema LD. M. Hiemstra H. Semeyn C. Speckamp WN. Tetrahedron 1994; 50: 7115
    • 20a Lolkema LD. M. Hiemstra H. Mooiweer HH. Speckamp WN. Tetrahedron Lett. 1988; 29: 6365
    • 20b Crosby SR. Harding JR. King CD. Parker GD. Willis CL. Org. Lett. 2002; 4: 577
    • 20c Barry CS. Bushby N. Harding JR. Hughes RA. Parker GD. Roe R. Willis CL. Chem. Commun. 2005; 3727
    • 21a Muzart J. Tetrahedron 2007; 63: 7505
    • 21b Mann SE. Benhamou L. Sheppard TD. Synthesis 2015; 47: 3079
    • 21c Baiju TV. Gravel E. Doris E. Namboothiri IN. N. Tetrahedron Lett. 2016; 57: 3993
    • 22a Wickens ZK. Skakuj K. Morandi B. Grubbs RH. J. Am. Chem. Soc. 2014; 136: 890
    • 22b Kim KE. Li J. Grubbs RH. Stoltz BM. J. Am. Chem. Soc. 2016; 138: 13179
    • 23a Cornell CN. Sigman MS. J. Am. Chem. Soc. 2005; 127: 2796
    • 23b Chaudhari DA. Fernandes RA. J. Org. Chem. 2016; 81: 2113
    • 23c Xia X. Gao X. Xu J. Hu C. Peng X. Synlett 2017; 28: 607