Synthesis 2016; 48(24): 4509-4518
DOI: 10.1055/s-0035-1562536
paper
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Synthesis of 2Z,4E-Configured Dienoates through Tethered Ring Closing Metathesis

Bernd Schmidt*
Universitaet Potsdam, Institut fuer Chemie, Karl-Liebknecht-Strasse 24-25, 14476 Potsdam-Golm, Germany   Email: bernd.schmidt@uni-potsdam.de
,
Stephan Audörsch
Universitaet Potsdam, Institut fuer Chemie, Karl-Liebknecht-Strasse 24-25, 14476 Potsdam-Golm, Germany   Email: bernd.schmidt@uni-potsdam.de
,
Oliver Kunz
Universitaet Potsdam, Institut fuer Chemie, Karl-Liebknecht-Strasse 24-25, 14476 Potsdam-Golm, Germany   Email: bernd.schmidt@uni-potsdam.de
› Author Affiliations
Further Information

Publication History

Received: 14 June 2016

Accepted after revision: 19 July 2016

Publication Date:
31 August 2016 (online)


Abstract

A two-step sequence leading from racemic allylic alcohols and vinylacetic acid to ethyl (2Z,4E)-dienoates is described. The sequence involves Steglich esterification of the reactants, followed by a one-pot ring closing metathesis–base induced elimination–alkylation reaction to furnish the products in high stereoselectivity. Trapping of the intermediate sodium carboxylates is accomplished efficiently using Meerwein’s salt Et3OBF4.

Supporting Information

 
  • References

  • 1 De Paolis M, Chataigner I, Maddaluno J. Top. Curr. Chem. 2012; 327: 87
  • 2 Gustafson K, Roman M, Fenical W. J. Am. Chem. Soc. 1989; 111: 7519
  • 3 Paterson I, Dalby SM, Roberts JC, Naylor GJ, Guzmán EA, Isbrucker R, Pitts TP, Linley P, Divlianska D, Reed JK, Wright AE. Angew. Chem. Int. Ed. 2011; 50: 3219
  • 4 Smith AB. III, Ott GR. J. Am. Chem. Soc. 1998; 120: 3935
  • 5 Paterson I, Ng KK. H, Williams S, Millican DC, Dalby SM. Angew. Chem. Int. Ed. 2014; 53: 2692
  • 6 Kim Y, Singer RA, Carreira EM. Angew. Chem. Int. Ed. 1998; 37: 1261
  • 7 Vintonyak VV, Kunze B, Sasse F, Maier ME. Chem. Eur. J. 2008; 14: 11132
  • 8 Marino JP, McClure MS, Holub DP, Comasseto JV, Tucci FC. J. Am. Chem. Soc. 2002; 124: 1664
  • 9 Mailhol D, Willwacher J, Kausch-Busies N, Rubitski EE, Sobol Z, Schuler M, Lam M.-H, Musto S, Loganzo F, Maderna A, Fürstner A. J. Am. Chem. Soc. 2014; 136: 15719
  • 10 Souris C, Misale A, Chen Y, Luparia M, Maulide N. Org. Lett. 2015; 17: 4486
  • 11 Funk TW, Efskind J, Grubbs RH. Org. Lett. 2005; 7: 171
  • 12 Andrade RB, Martin SF. Org. Lett. 2005; 7: 5733
  • 13 Morita A, Kuwahara S. Tetrahedron Lett. 2007; 48: 3163
  • 14 Moura-Letts G, Curran DP. Org. Lett. 2007; 9: 5
  • 15 Steinhardt SE, Silverston JS, Vanderwal CD. J. Am. Chem. Soc. 2008; 130: 7560
  • 16 Gallenkamp D, Fürstner A. J. Am. Chem. Soc. 2011; 133: 9232
  • 17 Sirasani G, Paul T, Andrade RB. Tetrahedron 2011; 67: 2197
  • 18 Paul T, Andrade RB. Tetrahedron Lett. 2007; 48: 5367
  • 19 Trost BM, Gunzner JL, Dirat O, Rhee YH. J. Am. Chem. Soc. 2002; 124: 10396
  • 20 Murelli RP, Snapper ML. Org. Lett. 2007; 9: 1749
  • 21 Schmidt B, Kunz O. Eur. J. Org. Chem. 2012; 1008
  • 22 Schmidt B, Kunz O. Beilstein J. Org. Chem. 2013; 9: 2544
  • 23 Schmidt B, Hauke S, Krehl S, Kunz O. Ring Closing Metathesis . In Comprehensive Organic Synthesis . 2nd ed., Vol. 5; Molander GA, Knochel P. Elsevier; Oxford: 2014: 1400-1482
  • 24 Bracegirdle S, Anderson EA. Chem. Soc. Rev. 2010; 39: 4114
  • 25 Čusak A. Chem. Eur. J. 2012; 18: 5800
  • 26 Bodugam M, Javed S, Ganguly A, Torres J, Hanson PR. Org. Lett. 2016; 18: 516
  • 27 Maitra S, Markley JL, Chegondi R, Hanson PR. Tetrahedron 2015; 71: 5734
  • 28 Scholl M, Ding S, Lee CW, Grubbs RH. Org. Lett. 1999; 1: 953
  • 29 ter Wiel MK. J, Kwit MG, Meetsma A, Feringa BL. Org. Biomol. Chem. 2007; 5: 87
  • 30 Meerwein H, Hinz G, Hofmann P, Kroning E, Pfeil E. J. Prakt. Chem. 1937; 147: 257
  • 31 Raber DJ, Gariano P, Brod AO, Gariano A, Guida WC, Guida AR, Herbst MD. J. Org. Chem. 1979; 44: 1149
  • 32 Seiders TJ, Ward DW, Grubbs RH. Org. Lett. 2001; 3: 3225
  • 33 Meng X, Matson JB, Edgar KJ. Biomacromolecules 2014; 15: 177
  • 34 Meerwein H, Delfs D, Morschel H. Angew. Chem. 1960; 72: 927
  • 35 Fürstner A, Langemann K. Synthesis 1997; 792
  • 36 Neises B, Steglich W. Angew. Chem., Int. Ed. Engl. 1978; 17: 522
  • 37 Stambasky J, Kapras V, Stefko M, Kysilka O, Hocek M, Malkov AV, Kocovsky P. J. Org. Chem. 2011; 76: 7781
  • 38 Sarkar N, Ghosh S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2006; 45: 2474
  • 39 Reddy GP, Reddy JS, Das S, Roisnel T, Yadav JS, Chandrasekhar S, Grée R. Org. Lett. 2013; 15: 1524
  • 40 Kempter I, Frensch B, Kopf T, Kluge R, Csuk R, Svoboda I, Fuess H, Hartung J. Tetrahedron 2014; 70: 1918
  • 41 Rabe P, Klapschinski TA, Brock NL, Citron CA, D’Alvise P, Gram L, Dickschat JS. Beilstein J. Org. Chem. 2014; 10: 1796
  • 42 Ahlsten N, Bartoszewicz A, Agrawal S, Martín-Matute B. Synthesis 2011; 2600
  • 43 Glattfeld JW. E, Hoen RE. J. Am. Chem. Soc. 1935; 57: 1405
  • 44 Schmidt B, Hauke S. Beilstein J. Org. Chem. 2014; 10: 1023
  • 45 Arlt D, Bieniek M, Karch R. EP 2066443, 2009
  • 46 Aranha RM, Bowser AM, Madalengoitia JS. Org. Lett. 2009; 11: 575
  • 47 Dess DB, Martin JC. J. Am. Chem. Soc. 1991; 113: 7277
  • 48 Kowalski CJ, Fields KW. J. Am. Chem. Soc. 1982; 104: 321
  • 49 Kowalski CJ, Haque MS, Fields KW. J. Am. Chem. Soc. 1985; 107: 1429
  • 50 Kowalski CJ, Reddy RE. J. Org. Chem. 1992; 57: 7194
  • 51 Maltese F, van der Krooy F, Verpoorte R. Nat. Prod. Commun. 2009; 4: 447
  • 52 Wnuk SF, Ro B.-O, Valdez CA, Lewandowska E, Valdez NX, Sacasa PR, Yin D, Zhang J, Borchardt RT, De Clercq E. J. Med. Chem. 2002; 45: 2651
  • 53 Mu L.-H, Wang B, Ren H.-Y, Liu P, Guo D.-H, Wang F.-M, Bai L, Guo Y.-S. Bioorg. Med. Chem. Lett. 2012; 22: 3343
  • 54 Shimizu S, Yoshihara S. Agric. Biol. Chem. 1977; 41: 1525
  • 55 Adelin E, Servy C, Cortial S, Lévaique H, Martin M.-T, Retailleau P, Le Goff G, Bussaban B, Lumyong S, Ouazzani J. Phytochemistry 2011; 72: 2406
  • 56 Tsuda M, Mugishima T, Komatsu K, Sone T, Tanaka M, Mikami Y, Kobayashi J.-i. J. Nat. Prod. 2003; 66: 412
  • 57 Sommart U, Rukachaisirikul V, Tadpetch K, Sukpondma Y, Phongpaichit S, Hutadilok-Towatana N, Sakayaroj J. Tetrahedron 2012; 68: 10005
  • 58 Hernández AS, Thaler A, Castells J, Rapoport H. J. Org. Chem. 1996; 61: 314