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Synthesis 2011(13): 2136-2146  
DOI: 10.1055/s-0030-1260053
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

1,3-Dipolar Cycloaddition on Baylis-Hillman Adducts: Novel Synthesis of Pyrrolidines, Spiropyrrolidines, and Spiropyrrolizidines

Manickam Bakthadoss*a, Nagappan Sivakumara, Anthonisamy Devaraja, Duddu S. Sharadab
a Dept. of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Fax: +91(44)22352494; e-Mail: bhakthadoss@yahoo.com;
b Organic Chemistry Division, Central Leather Research Institute, Adyar, Chennai 600 020, Tamil Nadu, India
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Publication History

Received 12 February 2011
Publication Date:
19 May 2011 (online)

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Abstract

A facile regio- and stereoselective synthesis of functionalized pyrrolidines, spiropyrrolidines, and spiropyrrolizidines using the Baylis-Hillman adducts derived from nitroolefins via intermolecular [3+2]-cycloaddition reaction is reported.

Key words

Baylis-Hillman reaction - intermolecular [3+2] cycloaddition - azomethine ylides - 1,3-dipolar cycloaddition - pyrrolidines - spiro compounds

    References

  • 1 Basavaiah D. Reddy BS. Badsara BS. Chem. Rev.  2010,  110:  5447 
    Search in Google Scholar
  • 2a Declerck V. Martinez J. Lamaty F. Chem. Rev.  2009,  109:  1 
    Search in Google Scholar
  • 2b Singh V. Batra S. Tetrahedron  2008,  64:  4511 
    Search in Google Scholar
  • 2c Basavaiah D. Rao KV. Reddy RJ. Chem. Soc. Rev.  2007,  36:  1581 
    Search in Google Scholar
  • 2d Masson G. Housseman C. Zhu J. Angew. Chem. Int. Ed.  2007,  46:  4614 
    Search in Google Scholar
  • 2e Basavaiah D. Rao AJ. Satyanarayana T. Chem. Rev.  2003,  103:  811 
    Search in Google Scholar
  • 2f Ciganek E. Org. React.  1997,  51:  201 
    Search in Google Scholar
  • 2g Auvray P. Knochel P. Normant JF. Tetrahedron Lett.  1986,  27:  5095 
    Search in Google Scholar
  • 2h Prasad BAS. Knochel P. Tetrahedron  1997,  53:  16711 
    Search in Google Scholar
  • 2i Basavaiah D. Rao PD. Hyma RS. Tetrahedron  1996,  52:  8001 
    Search in Google Scholar
  • 2j Drewes SE. Roos GHP. Tetrahedron  1988,  44:  4653 
    Search in Google Scholar
  • 3a Ma GN. Jiang JJ. Shi M. Wei Y. Chem. Commun.  2009,  5496 
  • 3b Amarante GW. Milagre HM. Vaz SBG. Ferreira BRV. Eberlin MN. Coelho F. J. Org. Chem.  2009,  74:  3031 
    Search in Google Scholar
  • 3c Trofimov A. Gevorgyan V. Org. Lett.  2009,  11:  253 
    Search in Google Scholar
  • 3d Deb I. Shanbhag P. Mobin SM. Namboothiri INN. Eur. J. Org. Chem.  2009,  4091 
  • 3e Krafft ME. Haxell TFN. Seibert KA. Abboud KA. J. Am. Chem. Soc.  2006,  128:  4174 
    Search in Google Scholar
  • 3f Turki T. Villieras J. Amri H. Tetrahedron Lett.  2005,  46:  3071 
    Search in Google Scholar
  • 3g Back TG. Rankic DA. Sorbetti JM. Wulff JE. Org. Lett.  2005,  7:  2377 
    Search in Google Scholar
  • 3h Nair V. Abhilash KG. Synthesis  2005,  1967 
  • 3i Jellerichs BG. Kong JR. Krische MJ. J. Am. Chem. Soc.  2003,  125:  7758 
    Search in Google Scholar
  • 3j Basavaiah D. Sreenivasalu B. Rao AJ. J. Org. Chem.  2003,  68:  5983 
    Search in Google Scholar
  • 3k Basavaiah D. Bakthadoss M. Jayapal Reddy G. Synthesis  2001,  919 
  • 3l Li G. Gao J. Wei HX. Enright M. Org. Lett.  2000,  2:  617 
    Search in Google Scholar
  • 3m Yang KS. Chen K. Org. Lett.  2000,  2:  729 
    Search in Google Scholar
  • 3n Basavaiah D. Gowriswari VVL. Bharathi TK. Tetrahedron Lett.  1987,  28:  4591 
    Search in Google Scholar
  • 3o Amri H. Villieras J. Tetrahedron Lett.  1986,  27:  4307 
    Search in Google Scholar
  • 4a Gendrineau T. Demoulin N. Navarre L. Genet J.-P. Darses S. Chem. Eur. J.  2009,  15:  4710 
    Search in Google Scholar
  • 4b Yadav LDS. Awasthi C. Tetrahedron Lett.  2009,  50:  3801 
    Search in Google Scholar
  • 4c Singh V. Batra S. Eur. J. Org. Chem.  2008,  5446 
  • 4d Shafiq Z. Liu L. Liu Z. Wang D. Chen YJ. Org. Lett.  2007,  9:  2525 
    Search in Google Scholar
  • 4e Lee SI. Hwang GS. Shin SC. Lee TG. Jo RH. Ryu DH. Org. Lett.  2007,  9:  5087 
    Search in Google Scholar
  • 4f Gowrisankar S. Lee KY. Lee CG. Kim JN. Tetrahedron Lett.  2004,  45:  6141 
    Search in Google Scholar
  • 4g Kabalka GW. Venkataiah B. Dong G. J. Org. Chem.  2004,  69:  5807 
    Search in Google Scholar
  • 4h Basavaiah D. Reddy RM. Tetrahedron Lett.  2001,  42:  3025 
    Search in Google Scholar
  • 4i Basavaiah D. Sarma PKS. J. Chem. Soc., Chem. Commun.  1992,  955 
  • 4j Bode ML. Kaye PT.
    J. Chem. Soc., Perkin Trans. 1  1990,  2612 
  • 5 Zeni G. Larock RC. Chem. Rev.  2006,  106:  4644 
    CrossrefPubMedSearch in Google Scholar
  • 6 Basavaiah D. Roy S. Org. Lett.  2008,  10:  1819 
    CrossrefSearch in Google Scholar
  • 7 Savitha G. Niveditha SK. Muralidharan D. Perumal PT. Tetrahedron Lett.  2007,  48:  2943 
    CrossrefSearch in Google Scholar
  • 8a Muthusamy S. Gunanathan C. Babu SA. Tetrahedron Lett.  2001,  42:  523 
    Search in Google Scholar
  • 8b Shanmugam P. Viswambharan B. Madhavan S. Org. Lett.  2007,  9:  4095 
    Search in Google Scholar
  • 9a Lown JW. In 1,3-Dipolar Cycloaddition Chemistry   Vol. 1:  Padwa A. Wiley; New York: 1984.  p.2 
    Search in Google Scholar
  • 9b Najera C. Sansano JM. Angew. Chem. Int. Ed.  2005,  44:  6272 
    Search in Google Scholar
  • 9c Gothelf KV. In Cycloaddition Reactions in Organic Synthesis   Kobayashi S. Jørgensen KA. Wiley-VCH; Weinheim: 2002.  p.211 
  • 9d Gothelf KV. Jørgensen KA. Chem. Rev.  1998,  98:  863 
    Search in Google Scholar
  • 10a Cordell GA. The Alkaloids: Chemistry and Biology   Academic Press; San Diego: 1998. 
  • 10b Cui C.-B. Kakeya H. Osada H. Tetrahedron  1996,  52:  12651 
    Search in Google Scholar
  • 10c Xue J. Zhang Y. Wang X.-I. Fun HK. Xu JH. Org. Lett.  2000,  2:  2583 
    Search in Google Scholar
  • 10d Klumpp DA. Yeung KY. Prakash GKS. Olah GA. J. Org. Chem.  1998,  63:  4481 
    Search in Google Scholar
  • 11a Jossang A. Jossang P. Hadi HA. Sevenet T. Bodo B. J. Org. Chem.  1991,  56:  6527 
    Search in Google Scholar
  • 11b Wong WH. Lim PB. Chuah CH. Phytochemistry  1996,  41:  313 
    Search in Google Scholar
  • 11c Dideberg O. Lamotte-Brasseur J. Dupont L. Campsteyn H. Vermeire M. Angenot L. Acta Crystallogr., Sect. B  1977,  33:  1796 
    Search in Google Scholar
  • 11d Cui CB. Kakeya H. Okada G. Onose R. Osada H. J. Antibiot.  1996,  49:  527 
    Search in Google Scholar
  • 11e Bindra JS. The Alkaloids   Vol. 14:  Manske RHF. Academic Press; New York: 1973.  p.84 
    Search in Google Scholar
  • 11f Lin H. Danishefky S. Angew. Chem. Int. Ed.  2003,  42:  36 
    Search in Google Scholar
  • 12a Fejes I. Toke L. Blasko G. Nyerges M. Pak CS. Tetrahedron  2000,  56:  8545 
    Search in Google Scholar
  • 12b Nyerges M. Bitter I. Kadas I. Toth G. Toke L. Tetrahedron  1995,  51:  11489 
    Search in Google Scholar
  • 12c Rang HP. Dale MM. Pharmacology   Churchill Livingstone; Edinburgh: 1991. 
  • 12d Song C. Leonard BE. Fundamentals of Psychoneuroimmunology   John Wiley; Chichester: 2000. 
  • 12e Albert A. Selective Toxicity   Chapman and Hall; London: 1985. 
  • 13a De Amici M. De Michelli C. Sani VM. Tetrahedron  1990,  46:  1975 
    Search in Google Scholar
  • 13b Early WG. Oh T. Overman LE. Tetrahedron Lett.  1988,  29:  3785 
    Search in Google Scholar
  • 13c Kozikowski AP. Acc. Chem. Res.  1984,  17:  410 
    Search in Google Scholar
  • 13d Ban Y. Taga N. Oishi T. Chem. Pharm. Bull.  1976,  24:  736 
    Search in Google Scholar
  • 13e Van Tamlen EE. Yardley JP. Miyano M. Hinshaw WB. J. Am. Chem. Soc.  1969,  91:  7333 
    Search in Google Scholar
  • 13f Howe RK. Shelton BR. J. Org. Chem.  1990,  55:  4603 
    Search in Google Scholar
  • 13g Cohan VL, and Kleinman EE. inventors; WO  9,524,398.  ; Chem. Abstr. 1995, 122, 20667j
  • 13h Ban Y. Seto M. Oishi T. Chem. Pharm. Bull.  1975,  23:  2605 
    Search in Google Scholar
  • 13i Ban Y. Taga N. Oishi T. Tetrahedron Lett.  1974,  15:  187 
    Search in Google Scholar
  • 13j Caroll WA. Grieco PA. J. Am. Chem. Soc.  1993,  115:  1164 
    Search in Google Scholar
  • 14 Ding K. Lu Y. Nikolovska-Coleska Z. Wang G. Qiu S. Shangary S. Gao W. Qin D. Stuckey J. Krajewski K. Roller PP. Wang S. J. Med. Chem.  2006,  49:  3432 
    CrossrefPubMedSearch in Google Scholar
  • 15a Hilton ST. Ho TCT. Pljevaljcic G. Jones K. Org. Lett.  2000,  2:  2639 
    Search in Google Scholar
  • 15b Coldham I. Hufton R. Chem. Rev.  2005,  105:  2765 
    Search in Google Scholar
  • 15c Pandey G. Banerjee P. Gadre SR. Chem. Rev.  2006,  106:  4484 
    Search in Google Scholar
  • 16a Daly JW. Spande TWF. Whittaker N. Highet RJ. Feigl D. Nishimori T. Tokuyama T. Myers CW.
    J. Nat. Prod.  1986,  49:  265 
    Search in Google Scholar
  • 16b Hilton ST. Ho TCT. Pljevaljcic G. Jones K. Org. Lett.  2000,  2:  2639 
    Search in Google Scholar
  • 16c Liddell JR. Nat. Prod. Rep.  1996,  13:  187 
    Search in Google Scholar
  • 16d Liddell JR. Nat. Prod. Rep.  1997,  14:  653 
    Search in Google Scholar
  • 16e Marti C. Carreira EM. Eur. J. Org. Chem.  2003,  2209 
  • 16f Toyota M. Ihara M. Nat. Prod. Rep.  1998,  15:  327 
    Search in Google Scholar
  • 16g Dounary AB. Hatanaka K. Kodanko JJ. Oestreich M. Pfeifer LA. Weiss MM. J. Am. Chem. Soc.  2003,  125:  6261 ; and references therein
    Search in Google Scholar
  • 17a Baylis AB, and Hillman MED. inventors; DE  2,155,113.  ; Chem. Abstr. 1972, 77, 34174q
  • 17b Rastogi N. Namboothiri INN. Cojocaru M. Tetrahedron Lett.  2004,  45:  4745 
    Search in Google Scholar
  • 18a Bakthadoss M. Sivakumar G. Kannan D. Org. Lett.  2009,  11:  4466 
    Search in Google Scholar
  • 18b Bakthadoss M. Murugan G. Eur. J. Org. Chem.  2010,  5825 
  • 18c Bakthadoss M. Sivakumar N. Devaraj A. Synthesis  2011,  611 
  • 18d Bakthadoss M. Sivakumar N. Synlett  2009,  1014 
  • 18e Bakthadoss M. Sivakumar N. Sivakumar G. Murugan G. Tetrahedron Lett.  2008,  49:  820 
    Search in Google Scholar
  • 18f Bakthadoss M. Murugan G. Synth. Commun.  2008,  38:  3406 
    Search in Google Scholar
  • 18g Bakthadoss M. Murugan G. Synth. Commun.  2009,  39:  1290 
    Search in Google Scholar
19

The X-ray crystal structure data of 8d, 9a, 10d, and 11a have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition numbers CCDC 812105 (8d), 676397 (9a), 676668 (10d), and 812104 (11a).