Synthesis 2014; 46(19): 2601-2607
DOI: 10.1055/s-0034-1378321
paper
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Construction of Functionalized Cyclopentanes by a Relay Ring-Closing Metathesis and Chiral Amine (Thio)urea-Promoted Michael Addition

Yinan Zhang
Department of Chemistry and Chemical Biology, University of New Mexico, , Albuquerque, NM 87131-0001, USA   Fax: +1(505)2772609   eMail: wwang@unm.edu
,
Xixi Song
Department of Chemistry and Chemical Biology, University of New Mexico, , Albuquerque, NM 87131-0001, USA   Fax: +1(505)2772609   eMail: wwang@unm.edu
,
Xiaobei Chen
Department of Chemistry and Chemical Biology, University of New Mexico, , Albuquerque, NM 87131-0001, USA   Fax: +1(505)2772609   eMail: wwang@unm.edu
,
Aiguo Song
Department of Chemistry and Chemical Biology, University of New Mexico, , Albuquerque, NM 87131-0001, USA   Fax: +1(505)2772609   eMail: wwang@unm.edu
,
Shilei Zhang
Department of Chemistry and Chemical Biology, University of New Mexico, , Albuquerque, NM 87131-0001, USA   Fax: +1(505)2772609   eMail: wwang@unm.edu
,
Wei Wang*
Department of Chemistry and Chemical Biology, University of New Mexico, , Albuquerque, NM 87131-0001, USA   Fax: +1(505)2772609   eMail: wwang@unm.edu
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 06. Mai 2014

Accepted after revision: 22. Mai 2014

Publikationsdatum:
24. Juni 2014 (online)


Abstract

A relay strategy is described that permits ring-closing metathesis and bifunctional chiral amine (thio)urea-catalyzed Michael­ addition reactions to proceed in a one-pot fashion. The process offers an alternative approach to the synthesis of structurally diverse chiral cyclopentanes in good yields and good enantioselectivities.

 
  • References


    • For recent reviews on organocatalyzed cascade reactions, see:
    • 2a Enders D, Grondal C, Hüttl MR. Angew. Chem. Int. Ed. 2007; 46: 1570
    • 2b Guillena G, Ramón DJ, Yus M. Tetrahedron: Asymmetry 2007; 18: 693
    • 2c Yu X, Wang W. Org. Biomol. Chem. 2008; 6: 2037
    • 2d Wu L.-Y, Bencivenni G, Mancinelli M, Mazzanti A, Bartoli G, Melchiorre P. Angew. Chem. Int. Ed. 2009; 48: 7196
    • 2e Alba A.-N, Companyo X, Viciano M, Rios R. Curr. Org. Chem. 2009; 13: 1432
    • 2f Grondal C, Jeanty M, Enders D. Nat. Chem. 2010; 2: 167
    • 2g Westermann B, Ayaz M, van Berkel SS. Angew. Chem. Int. Ed. 2010; 49: 846
    • 2h Peng F.-Z, Shao Z.-H. Curr. Org. Chem. 2011; 15: 4144
    • 2i Ruiz M, López-Alvarado P, Giorgi G, Menéndez JC. Chem. Soc. Rev. 2011; 40: 3445
    • 2j Pellissier H. Adv. Synth. Catal. 2012; 354: 237
  • 3 MacMillan DW. C. Nature 2008; 455: 304

    • For reviews on combining organocatalysis with metal catalysis, see:
    • 4a Shao Z, Zhang H. Chem. Soc. Rev. 2009; 38: 2745
    • 4b de Armas P, Tejedor D, García-Tellado F. Angew. Chem. Int. Ed. 2010; 49: 1013
    • 4c Zhong C, Shi X.-D. Eur. J. Org. Chem. 2010; 2999
    • 4d Rueping M, Koenigs RM, Atodiresei I. Chem. Eur. J. 2010; 16: 9350
    • 4e Zhou J. Chem. Asian J. 2010; 5: 422
    • 4f Han Z.-Y, Wang C, Gong L.-Z In Science of Synthesis: Asymmetric Organocatalysis . Vol. 2. Maruoka K. Thieme; Stuttgart: 2012: 697
    • 4g Loh CC. J, Enders D. Chem. Eur. J. 2012; 18: 10212
    • 4h Allen AE, MacMillan DW. C. Chem. Sci. 2012; 3: 633
    • 4i Patil NT, Shinde VS, Gajula B. Org. Biomol. Chem. 2012; 10: 211
    • 4j Pellissier H. Tetrahedron 2013; 69: 7171
    • 4k Du Z.-T, Shao Z.-H. Chem. Soc. Rev. 2013; 42: 1337
    • 5a Chauvin Y. Angew. Chem. Int. Ed. 2006; 45: 3740
    • 5b Grubbs RH. Angew. Chem. Int. Ed. 2006; 45: 3760
  • 6 Sorimachi K, Terada M. J. Am. Chem. Soc. 2008; 130: 14452
  • 7 Simmons B, Walji AM, MacMillan DW. C. Angew. Chem. Int. Ed. 2009; 48: 4349
    • 8a Cai Q, Zhao Z.-A, You S.-L. Angew. Chem. Int. Ed. 2009; 48: 7428
    • 8b Zhang J.-W, Cai Q, Gu Q, Shi X.-X, You S.-L. Chem. Commun. 2013; 49: 7750
    • 8c Cai Q, Liang X.-W, Wang S.-G, You S.-L. Org. Biomol. Chem. 2013; 11: 1602
    • 9a Chen J.-R, Li C.-F, An X.-L, Zhang J.-J, Zhu X.-Y, Xiao W.-J. Angew. Chem. Int. Ed. 2008; 47: 2489
    • 9b An X.-L, Chen J.-R, Li C.-F, Zhang F.-G, Zou Y.-Q, Guo Y.-C, Xiao W.-J. Chem. Asian J. 2010; 5: 2258

      For recent reviews on catalysis by bifunctional (thio)ureas, see ref. 1c and:
    • 10a Akiyama T, Itoh J, Fuchibe K. Adv. Synth. Catal. 2006; 348: 999
    • 10b Connon SJ. Chem. Eur. J. 2006; 12: 5418
    • 10c Marcelli T, van Maarseveen JH, Hiemstra H. Angew. Chem. Int. Ed. 2006; 45: 7496
    • 10d Colby Davie EA, Mennen SM, Xu Y, Miller SJ. Chem. Rev. 2007; 107: 5759
    • 10e List B. Chem. Rev. 2007; 107: 5413
    • 10f Doyle AG, Jacobsen EN. Chem. Rev. 2007; 107: 5713
    • 10g Zhang Z, Schreiner PR. Chem. Soc. Rev. 2009; 38: 1187
    • 10h Takemoto Y. Chem. Pharm. Bull. 2010; 58: 593
    • 10i Hof K, Lippert M, Schreiner PR. In: Science of Synthesis: Asymmetric Organocatalysis . Vol. 2. Maruoka K. Thieme; Stuttgart: 2012: 297
    • 10j Serdyuk OV, Heckel CM, Tsogoeva SB. Org. Biomol. Chem. 2013; 11: 7051
    • 11a Zu L, Li H, Xie H, Wang J, Jiang W, Tang T, Wang W. Angew. Chem. Int. Ed. 2007; 46: 3732
    • 11b Wang JW, Li H, Xie H, Zu L, Shen X, Wang W. Angew. Chem. Int. Ed. 2007; 46: 9050
    • 12a Okino T, Hoashi Y, Furukawa T, Xu X, Takemoto Y. J. Am. Chem. Soc. 2005; 127: 119
    • 12b Vakulya B, Varga S, Csámpai A, Soós T. Org. Lett. 2005; 7: 1967
    • 12c Wang J, Li H, Zu L.-S, Jiang W, Xie H, Duan W, Wang W. J. Am. Chem. Soc. 2006; 128: 12652
  • 13 Crystallographic data for compound 5 have been deposited with the accession number CCDC 986732, and can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk; Web site: www.ccdc.cam.ac.uk/conts/retrieving.html.