Synthesis 2015; 47(15): 2223-2232
DOI: 10.1055/s-0034-1378856
special topic
© Georg Thieme Verlag Stuttgart · New York

Nucleophilic Conjugate 1,5-Addition of Gilman Reagents to (E)-Hex-2-en-4-ynedioates: An Access to β(γ′)-Substituted Muconates

Hung-Che Tai
Department of Applied Chemistry, National Chiao Tung University, Hsinchu 30010, Taiwan   Email: jscchuang@faculty.nctu.edu.tw
,
Arjun S. Chavan
Department of Applied Chemistry, National Chiao Tung University, Hsinchu 30010, Taiwan   Email: jscchuang@faculty.nctu.edu.tw
,
Shih-Ching Chuang*
Department of Applied Chemistry, National Chiao Tung University, Hsinchu 30010, Taiwan   Email: jscchuang@faculty.nctu.edu.tw
› Author Affiliations
Further Information

Publication History

Received: 31 March 2015

Accepted after revision: 05 June 2015

Publication Date:
15 July 2015 (online)

Abstract

An unusual nucleophilic conjugate addition of organocu­prates to enynedioates resulted in chemo- and regioselective formation of β(γ′)-addition products, rather than α(δ′)-addition products, in moderate to good yields. This addition pattern is different from that with organophosphanes or alkyl amines, and presents a short and efficient method for the preparation of various β(γ′)-alkyl- or -aryl-substituted muconates compared with other synthetic approaches.

Supporting Information

 
  • References

  • 1 Csákÿ AG, de la Herrán G, Murcia MC. Chem. Soc. Rev. 2010; 39: 4080
  • 2 Smith MB. Organic Synthesis . McGraw-Hill Education; New York: 1994
  • 3 Gilman H, Jones RG, Woods LA. J. Org. Chem. 1952; 17: 1630
  • 4 Woodward S, Willcox D. In: Innovative Catalysis in Organic Synthesis: Oxidation, Hydrogenation, and C–X Bond Forming Reactions. Andersson PG. Wiley-VCH; Weinheim: 2012: 233
  • 5 Chounan Y, Yamamoto Y. In: Modern Organocopper Chemistry . Krause N. Wiley-VCH; Weinheim: 2002. Chap. 9, 289
  • 6 Krause N, Hoffmann-Röder A. Modern Organocopper Chemistry . Krause N. Wiley-VCH; Weinheim: 2002. Chap. 4, 145
  • 7 Corey EJ, Katzenellenbogen JA. J. Am. Chem. Soc. 1969; 91: 1851
  • 8 Zhu X.-F, Henry CE, Kwon O. J. Am. Chem. Soc. 2007; 129: 6722
  • 9 Ernst L, Hopf H, Krause N. J. Org. Chem. 1987; 52: 398
  • 10 Canisius J, Mobley TA, Berger S, Krause N. Chem. Eur. J. 2001; 7: 2671
  • 11 Tseng P.-Y, Chuang S.-C. Adv. Synth. Catal. 2013; 355: 2165
    • 12a Deng J.-C, Chuang S.-C. Org. Lett. 2011; 13: 2248
    • 12b Chuang S.-C, Deng J.-C, Chan F.-W, Chen S.-Y, Huang W.-J, Lai L.-H, Rajeshkumar V. Eur. J. Org. Chem. 2012; 2606
    • 12c Chavan AS, Deng J.-C, Chuang S.-C. Molecules 2013; 18: 2611
    • 12d Lin Y.-W, Deng J.-C, Hsieh Y.-Z, Chuang S.-C. Org. Biomol. Chem. 2014; 12: 162
    • 12e Winterfeldt E, Preuss H. Chem. Ber. 1966; 99: 450
    • 12f Zhou L.-H, Yu X.-Q, Pu L. Tetrahedron Lett. 2010; 51: 425
    • 12g Han Y, Sheng Y.-J, Yan C.-G. Org. Lett. 2014; 16: 2654
    • 12h Deng J.-C, Chen W.-Y, Zhu C, Chuang S.-C. Adv. Synth. Catal. 2015; 357: 1453
  • 13 Deng J.-C, Chuang S.-C. Org. Lett. 2014; 16: 5792
  • 14 Deng J.-C, Kuo C.-W, Chuang S.-C. Chem. Commun. 2014; 50: 10580
  • 15 Takao K, Munakata R, Tadano K.-i. Chem. Rev. 2005; 105: 4779
  • 16 Fink JK. Reactive Polymers: Fundamentals and Applications: A Concise Guide to Industrial Polymers. William Andrew; Norwich: 2005: 573
  • 17 Tori M, Sono M, Takikawa K, Matsuda R, Toyota M, Cheminat A, Asakawa Y. J. Chem. Res., Synop. 1999; 470
  • 18 Le Paih J, Vovard-Le Bray C, Dérien S, Dixneuf PH. J. Am. Chem. Soc. 2010; 132: 7391
  • 19 Neisius NM, Plietker B. Angew. Chem. Int. Ed. 2009; 48: 5752
  • 20 Shibata Y, Hirano M, Tanaka K. Org. Lett. 2008; 10: 2829
  • 21 Stephen H, Weizmann C. J. Chem. Soc., Trans. 1913; 103: 269
    • 22a Hu X.-H, Zhang J, Yang X.-F, Xu Y.-H, Loh T.-P. J. Am. Chem. Soc. 2015; 137: 3169
    • 22b Xiao Q, Wang B, Tian L, Yang Y, Ma J, Zhang Y, Chen S, Wang J. Angew. Chem. Int. Ed. 2013; 52: 9305
  • 23 Ramachandran PV, Rudd MT, Reddy MV. R. Tetrahedron Lett. 2005; 46: 2547
  • 24 Acheson RM, Ansell PJ, Murray JR. J. Chem. Res., Synop. 1986; 378