Synthesis 2014; 46(16): 2161-2167
DOI: 10.1055/s-0033-1341204
special topic
© Georg Thieme Verlag Stuttgart · New York

Highly Diastereoselective Synthesis of Cyclopentenones via a One-Pot Gold Catalysis, Nazarov Cyclization and Alkylation Cascade

Meng-Qi Liu
State Key Laboratory for Physical Chemistry of Solid Surfaces, The Key Laboratory for Chemical Biology of Fujian Province and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, P. R. of China   Fax: +86(592)2185833   Email: longwuye@xmu.edu.cn
,
Ai-Hua Zhou
State Key Laboratory for Physical Chemistry of Solid Surfaces, The Key Laboratory for Chemical Biology of Fujian Province and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, P. R. of China   Fax: +86(592)2185833   Email: longwuye@xmu.edu.cn
,
Shuang Jiang
State Key Laboratory for Physical Chemistry of Solid Surfaces, The Key Laboratory for Chemical Biology of Fujian Province and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, P. R. of China   Fax: +86(592)2185833   Email: longwuye@xmu.edu.cn
,
Jia-Qi Wang
State Key Laboratory for Physical Chemistry of Solid Surfaces, The Key Laboratory for Chemical Biology of Fujian Province and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, P. R. of China   Fax: +86(592)2185833   Email: longwuye@xmu.edu.cn
,
Long-Wu Ye*
State Key Laboratory for Physical Chemistry of Solid Surfaces, The Key Laboratory for Chemical Biology of Fujian Province and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, P. R. of China   Fax: +86(592)2185833   Email: longwuye@xmu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 18 February 2014

Accepted: 21 March 2014

Publication Date:
09 April 2014 (eFirst)

Abstract

Starting from readily available propargylic carboxylates, three sequential transformations [gold-catalyzed tandem reaction, scandium(III) trifluoromethanesulfonate catalyzed Nazarov cyclization, alkylation reaction] in a one-pot process led to the formation of cyclopentenone derivatives in excellent diastereoselectivities and moderate to good overall yields.

Supporting Information

 
  • References


    • For recent reviews on the Nazarov reaction, see:
    • 1a Spencer III WT, Vaidya T, Frontier AJ. Eur. J. Org. Chem. 2013; 3621
    • 1b Audran G, Brémond P, Feuerstein M, Marque SR. A, Santelli M. Tetrahedron 2013; 69: 8325
    • 1c Vaidya T, Eisenberg R, Frontier AJ. ChemCatChem 2011; 3: 1531
    • 1d Shimada N, Stewart C, Tius MA. Tetrahedron 2011; 67: 5851
    • 1e Grant TN, Rieder CJ, West FG. Chem. Commun. 2009; 5676
    • 1f Nakanishi W, West FG. Curr. Opin. Drug Discovery Dev. 2009; 12: 732

      For selected work done by the Frontier research group, see:
    • 2a Vaidya T, Cheng R, Carlsen PN, Frontier AJ, Eisenberg R. Org. Lett. 2014; 16: 800
    • 2b Lebœuf D, Theiste E, Gandon V, Daifuku SL, Neidig ML, Frontier AJ. Chem. Eur. J. 2013; 19: 4842
    • 2c Lebœuf D, Gandon V, Ciesielski J, Frontier AJ. J. Am. Chem. Soc. 2012; 134: 6296
    • 2d Huang J, Lebœuf D, Frontier AJ. J. Am. Chem. Soc. 2011; 133: 6307
    • 2e Vaidya T, Manbeck GF, Chen S, Frontier AJ, Eisenberg R. J. Am. Chem. Soc. 2011; 133: 3300
    • 2f Lebœuf D, Huang J, Gandon V, Frontier AJ. Angew. Chem. Int. Ed. 2011; 50: 10981
    • 2g He W, Herrick IR, Atesin TA, Caruana PA, Kellenberger CA, Frontier AJ. J. Am. Chem. Soc. 2008; 130: 1003
    • 2h Janka M, He W, Frontier AJ, Eisenberg R. J. Am. Chem. Soc. 2004; 126: 6864
    • 2i He W, Sun X, Frontier AJ. J. Am. Chem. Soc. 2003; 125: 14278

      For other representative examples, see:
    • 3a Hoffmann M, Weibel J.-M, Frémont P, Pale P, Blanc A. Org. Lett. 2014; 16: 908
    • 3b Hutson GE, Türkmen YE, Rawal VH. J. Am. Chem. Soc. 2013; 135: 4988
    • 3c Xi Z.-G, Zhu L, Luo S, Cheng J.-P. J. Org. Chem. 2013; 78: 606
    • 3d Kerr DJ, Miletic M, Chaplin JH, White JM, Flynn BL. Org. Lett. 2012; 14: 1732
    • 3e Rueping M, Ieawsuwan W. Chem. Commun. 2011; 47: 11450
    • 3f Subramanium SS, Handa S, Miranda AJ, Slaughter LM. ACS Catal. 2011; 1: 1371
    • 3g Simone FD, Saget T, Benfatti F, Almeida S, Waser J. Chem. Eur. J. 2011; 17: 14527
    • 3h Cao P, Deng C, Zhou Y.-Y, Sun X.-L, Zheng J.-C, Xie Z.-W, Tang Y. Angew. Chem. Int. Ed. 2010; 49: 4463
    • 3i Yaji K, Shindo M. Synlett 2009; 2524

      For recent, selected reviews on gold catalysis, see:
    • 4a Zhang L. Acc. Chem. Res. 2014; 47: 877
    • 4b Wang Y.-M, Lackner AD, Toste FD. Acc. Chem. Res. 2014; 47: 889
    • 4c Brooner RE. M, Widenhoefer RA. Angew. Chem. Int. Ed. 2013; 52: 11714
    • 4d Rudolph M, Hashmi AS. K. Chem. Soc. Rev. 2012; 41: 2448
    • 4e Krause N, Winter C. Chem. Rev. 2011; 111: 1994
    • 4f Corma A, Leyva-Pérez A, Sabater MJ. Chem. Rev. 2011; 111: 1657
    • 4g Hirner JJ, Shi Y, Blum SA. Acc. Chem. Res. 2011; 44: 603
    • 4h Xiao J, Li X. Angew. Chem. Int. Ed. 2011; 50: 7226
    • 4i Fürstner A. Chem. Soc. Rev. 2009; 38: 3208
    • 4j Sohel SM. A, Liu R.-S. Chem. Soc. Rev. 2009; 38: 2269
    • 4k Patil NT, Yamamoto Y. Chem. Rev. 2008; 108: 3395
    • 4l Gorin DJ, Sherry BD, Toste FD. Chem. Rev. 2008; 108: 3351
    • 4m Jiménez-Núñez E, Echavarren AM. Chem. Rev. 2008; 108: 3326
    • 4n Arcadi A. Chem. Rev. 2008; 108: 3266
    • 4o Li Z, Brouwer C, He C. Chem. Rev. 2008; 108: 3239
    • 4p Bongers N, Krause N. Angew. Chem. Int. Ed. 2008; 47: 2178
    • 4q Hashmi AS. K, Rudolph M. Chem. Soc. Rev. 2008; 37: 1766
  • 5 Wang S, Zhang L. J. Am. Chem. Soc. 2006; 128: 8414

    • For selected reviews on the one-pot reactions, see:
    • 6a Patil NT, Shinde VS, Gajula B. Org. Biomol. Chem. 2012; 10: 211
    • 6b Climent MJ, Corma A, Iborra S. Chem. Rev. 2011; 111: 1072
    • 6c Albrecht Ł, Jiang H, Jørgensen KA. Angew. Chem. Int. Ed. 2011; 50: 8492
    • 6d Ramachary DB, Jain S. Org. Biomol. Chem. 2011; 9: 1277
    • 6e Wahba AE, Hamann MT. Mar. Drugs 2010; 8: 2395
    • 6f Hussain MM, Walsh PJ. Acc. Chem. Res. 2008; 41: 883
    • 6g Lee JM, Na Y, Han H, Chang S. Chem. Soc. Rev. 2004; 33: 302
  • 7 Cao S, Zhang L. Sci. China Chem. 2009; 52: 1337
  • 8 Yu M, Li G, Wang S, Zhang L. Adv. Synth. Catal. 2007; 349: 871
  • 9 Janka M, He W, Haedicke IE, Fronczek FR, Frontier AJ, Eisenberg R. J. Am. Chem. Soc. 2006; 128: 5312