Synlett 2014; 25(2): 280-282
DOI: 10.1055/s-0033-1340347
letter
© Georg Thieme Verlag Stuttgart · New York

A Tandem Conjugate Addition–Intramolecular Horner–Wadsworth–Emmons Olefination Approach to the Synthesis of Cyclopentene[c]chroman-2-ones and Cyclopent-1-enecarboxylates

Dariusz Deredas
a   Institute of Organic Chemistry, Technical University (Politechnika), Żeromskiego 116, 90-924 Łódź, Poland   Fax: +48(42)6365530   Email: henkrawc@p.lodz.pl
,
Krzysztof Huben
a   Institute of Organic Chemistry, Technical University (Politechnika), Żeromskiego 116, 90-924 Łódź, Poland   Fax: +48(42)6365530   Email: henkrawc@p.lodz.pl
,
Waldemar Maniukiewicz
b   Institute of General and Ecological Chemistry, Technical University (Politechnika), Żeromskiego 116, 90-924 Łódź, Poland
,
Henryk Krawczyk*
a   Institute of Organic Chemistry, Technical University (Politechnika), Żeromskiego 116, 90-924 Łódź, Poland   Fax: +48(42)6365530   Email: henkrawc@p.lodz.pl
› Author Affiliations
Further Information

Publication History

Received: 25 October 2013

Accepted after revision: 09 November 2013

Publication Date:
06 December 2013 (online)


Abstract

A strategically new approach to cyclopentene[c]chroman-2-ones and cyclopent-1-enecarboxylates by tandem Michael–Horner–Wadsworth–Emmons reaction of 2,5-hexanedione with 3-(diethoxyphosphoryl)coumarins is described. The products were obtained as single diastereoisomers in high yields.

Supporting Information

Primary Data

 
  • References and Notes

    • 1a Cane DE, Rossi T. Tetrahedron Lett. 1979; 2973
    • 1b Cane DE, Sohng J.-K, Williard PG. J. Org. Chem. 1992; 57: 844
    • 1c Giannetti BM, Steffan B, Steglich W, Kupka J, Anke T. Tetrahedron 1986; 42: 3587
    • 1d Kaneda M, Takahashi R, Itake Y, Shibata S. Tetrahedron Lett. 1972; 4609
    • 1e Groweiss A, Fenical W, Cun-Heng H, Clardy J. Tetrahedron Lett. 1985; 26: 2379
    • 2a Sakan T, Isoe S, Be Hyeon S, Katsumura R, Maeda T, Wolinsky J, Dickerson D, Slabaugh M, Nelson D. Tetrahedron Lett. 1965; 4097
    • 2b Sakan T, Murai F, Isoe S, Be Hyeon S, Hayashi Y. J. Chem. Soc. Jpn., Pure Chem. Sect. 1969; 90: 507
    • 2c Matsuo A, Yuki S, Nakayama M. J. Chem. Soc., Perkin Trans. 1 1986; 701
    • 2d Schuda PF. Top. Curr. Chem. 1980; 91: 75
    • 3a Neel M, Gouin J, Voituriez A, Marinetti A. Synthesis 2011; 2003
    • 3b Henry CE, Kwon O. Org. Lett. 2007; 9: 3069
    • 3c Kohn BL, Jarvo ER. Org. Lett. 2011; 13: 4858
    • 3d Tokuyama H, Isaka M, Nakamura E. J. Am. Chem. Soc. 1992; 114: 5523
    • 3e Trost BM, Mignani SM, Nanninga TN. J. Am. Chem. Soc. 1988; 110: 1602
    • 4a Minami T, Nakayama M, Fujimoto K, Matsuo S. Phosphorus, Sulfur Silicon Relat. Elem. 1993; 75: 135
    • 4b Bestmann HJ, Lehnen H. Tetrahedron Lett. 1991; 32: 4279
    • 4c Krawczyk H, Albrecht Ł. Synthesis 2008; 3951
    • 5a Werstiuk NH. Tetrahedron 1982; 39: 205
    • 5b Stowell JC. Chem. Rev. 1984; 84: 409
    • 5c Hudlicky T, Price JD. Chem. Rev. 1989; 89: 1467
    • 5d Nair V, Vellalath S, Babu BP. Chem. Soc. Rev. 2008; 37: 2691
  • 6 Deredas D, Albrecht Ł, Maniukiewicz W, Wojciechowski J, Wolf WM, Paluch P, Janecki T, Różalski M, Krajewska U, Janecka A, Krawczyk H. RSC Adv. 2013; 3: 6821
    • 7a Gould ES In Mechanism and Structure in Organic Chemistry . Holt, Rinehart, and Winston; New York: 1959: 331
    • 7b Lowry TH, Schueller Richardson K In Mechanism and Theory in Organic Chemistry . Harper and Row; New York: 1981. 2nd ed. 645
    • 7c Johnson SL In Advances in Physical Organic Chemistry . Academic Press; London/New York: 1967: 237
    • 7d Bender ML, Bergeron RJ, Komiyama M In The Bioorganic Chemistry of Enzymatic Catalysis . John Wiley and Sons; 1984. Chap. 7
    • 7e Deredas D, Albrecht Ł, Krawczyk H. Tetrahedron Lett. 2013; 54: 3088
  • 8 Crystallographic data (excluding structure factors) for the structure reported herein have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC 966779. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK. Any request should be accompanied by a full literature citation.