Synthesis 2017; 49(01): 167-174
DOI: 10.1055/s-0036-1588347
paper
© Georg Thieme Verlag Stuttgart · New York

Synergistic Catalysis: Asymmetric Synthesis of Cyclopentanes Bearing Four Stereogenic Centers

Kaiheng Zhang
School of Chemistry, University of Southampton, Highfield Campus, SO17 1BJ, UK
,
Marta Meazza
School of Chemistry, University of Southampton, Highfield Campus, SO17 1BJ, UK
,
Anabel Izaga
School of Chemistry, University of Southampton, Highfield Campus, SO17 1BJ, UK
Departamento de Química Inorgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza, 50009 Zaragoza, Spain
,
Clotilde Contamine
School of Chemistry, University of Southampton, Highfield Campus, SO17 1BJ, UK
Ecole Nationale Supérieure d’Ingénieurs de Caen, Ensicaen, 6, boulevard Maréchal Juin, CS 45053 14050 Caen, France
,
M. Concepción Gimeno
Departamento de Química Inorgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza, 50009 Zaragoza, Spain
,
Raquel P. Herrera
Laboratorio de Organocatálisis Asimétrica, Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza, 50009 Zaragoza, Spain   Email: rrt1f11@soton.ac.uk
,
Ramon Rios*
School of Chemistry, University of Southampton, Highfield Campus, SO17 1BJ, UK
› Author Affiliations
Further Information

Publication History

Received: 27 September 2016

Accepted after revision: 20 October 2016

Publication Date:
01 December 2016 (eFirst)

This paper is dedicated to Professor Dieter Enders on the occasion of his 70th birthday. He has always been a source of inspiration to develop new cascade reactions.

Abstract

We present a formal [3+2] cycloaddition based on synergistic catalysis. Vinylcyclopropanes derived from cyanoesters react with enals by dual activation using palladium(0) and secondary amines to form the corresponding cyclopentanes in good yields and stereoselectivities.

Supporting Information

 
  • References

    • 1a Allen A, MacMillan DW. C. Chem. Sci. 2012; 3: 633
    • 1b Meazza M, Rios R. Synthesis 2016; 48: 960
    • 2a Ibrahem I, Breistein P, Cordova A. Angew. Chem. Int. Ed. 2011; 50: 12036
    • 2b Ibrahem I, Ma G, Afewerki S, Cordova A. Angew. Chem. Int. Ed. 2013; 52: 878
    • 2c Ibrahem I, Santoro S, Himo F, Cordova A. Adv. Synth. Catal. 2011; 353: 245
    • 3a Jiang G, List B. Angew. Chem. Int. Ed. 2011; 50: 9471
    • 3b Jiang G, Halder R, Fang Y, List B. Angew. Chem. Int. Ed. 2011; 50: 9752
    • 3c Mukherjee S, List B. J. Am. Chem. Soc. 2007; 129: 11336
    • 3d Liao S, List B. Angew. Chem. Int. Ed. 2010; 49: 628
    • 3e Jiang G, List B. Adv. Synth. Catal. 2011; 353: 1667
    • 3f Jiang G, List B. Chem. Commun. 2011; 47: 10022
    • 4a Ceban V, Putaj P, Meazza M, Pitak MB, Coles SJ, Vesely J, Rios R. Chem. Commun. 2014; 50: 7447
    • 4b Meazza M, Ceban V, Pitak MB, Coles SJ, Rios R. Chem. Eur. J. 2014; 20: 16853
    • 4c Meazza M, Light ME, Mazzanti A, Rios R. Chem. Sci. 2016; 7: 984

      For reviews on organocascade reactions, see:
    • 5a Moyano A, Rios R. Chem. Rev. 2011; 111: 4703
    • 5b Alba A.-N, Companyo X, Viciano M, Rios R. Curr. Org. Chem. 2009; 13: 1432
    • 5c Enders D, Grondal C, Huettl MR. M. Angew. Chem. Int. Ed. 2007; 46: 1570 Angew. Chem. 2007, 119, 1590
    • 6a Laugeois M, Ponra S, Ratovelomanana-Vidal V, Michelet V, Vitale MR. Chem. Commun. 2016; 52: 5332
    • 6b Halskov KS, Naesborg L, Tur F, Jørgensen KA. Org. Lett. 2016; 16: 2220
    • 6c Meazza M, Rios R. Chem. Eur. J. 2016; 22: 9923
  • 7 Wang SC, Troast DM, Conda-Sheridan M, Zuo G, LaGarde D, Louie J, Tantillo DJ. J. Org. Chem. 2009; 74: 7822
    • 8a Dell’Amico L, Companyo X, Naicker T, Braeuer TM, Jørgensen KA. Eur. J. Org. Chem. 2013; 5262
    • 8b Li T, Zhu J, Wu D, Li X, Wang S, Li H, Li J, Wang W. Chem. Eur. J. 2013; 19: 9147
    • 8c Vesely J, Rios R, Ibrahem I, Zhao GL, Erickson L, Cordova A. Chem. Eur. J. 2008; 14: 2693
  • 9 Ma G, Afewerki S, Deiana L, Palo-Nieto C, Lie L, Sun J, Ibrahem I, Cordova A. Angew. Chem. Int. Ed. 2013; 52: 6050