Synlett 2010(6): 962-966  
DOI: 10.1055/s-0029-1219534
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

BINAP-AgSbF6 vs. BINAP-AgClO4 Complexes as Catalysts for the Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylides and Alkenes

María Martín-Rodrígueza, Carmen Nájeraa, José M. Sansano*a, Paulo R. R. Costab, Evanoel Crizanto de Limab, Ayres G. Diasb
a Departamento de Química Orgánica e Instituto de Síntesis Orgánica (ISO), Facultad de Ciencias, Universidad de Alicante, 03080 Alicante, Spain
Fax: +34(96)5903549; e-Mail: jmsansano@ua.es;
b Laboratório de Química Biorgânica, Núcleo de Pesquisas de Produtos Naturais, Centro de Ciencias da Saúde, Universidade Federal do Rio de Janeiro, Cidade Universitária, 21941-590 Rio de Janeiro, Brazil
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Publikationsverlauf

Received 30 December 2009
Publikationsdatum:
23. Februar 2010 (online)

Abstract

The employment of AgSbF6 and BINAP ligands has been evaluated in the catalyzed enantioselective 1,3-dipolar cycloadditions between azomethine ylides and electrophilic alkenes. The results are compared with the analogous ones obtained when using AgClO4. The cycloaddition with maleimides and trans-1,2-bis(phenylsulfonyl)ethylene are clearly improved by the AgSbF6-derived catalyst, and its efficiency is crucial for ensure good yields and excellent ee in the three-component reaction.

    References and Notes

  • For more general reviews of 1,3-dipolar cycloadditions, see:
  • 1a Padwa A. Bur SK. Tetrahedron  2007,  63:  5341 
  • 1b Pellisier H. Tetrahedron  2007,  63:  3235 
  • 1c Coldham I. Hufton R. Chem. Rev.  2005,  105:  2765 
  • 2 Longmire JM. Wang B. Zhang X. J. Am. Chem. Soc.  2002,  124:  13400 
  • For the first enantioselective 1,3-DC catalyzed by stoichiometric amounts of Ag+ complexes, see:
  • 3a Allway P. Grigg R. Tetrahedron Lett.  1991,  32:  5817 
  • 3b Grigg R. Tetrahedron: Asymmetry  1995,  6:  2475 
  • For recent reviews, see:
  • 4a Nájera C. Sansano JM. Topics in Heterocyclic Chemistry   Hassner A. Springer; New York: . 
  • 4b Stanley LM. Sibi MP. Chem. Rev.  2008,  108:  2887 
  • 4c Álvarez-Corral M. Muñoz-Dorado M. Rodríguez-García I. Chem. Rev.  2008,  108:  3174 
  • 4d Naodovic M. Yamamoto H. Chem. Rev.  2008,  108:  3132 
  • 4e Nair V. Suja TD. Tetrahedron  2007,  63:  12247 
  • 4f Pandey G. Banerjee P. Gadre SR. Chem. Rev.  2006,  106:  4484 
  • 4g Pinho e Melo TMVD. Eur. J. Org. Chem.  2006,  2873 
  • 4h Bonin M. Chauveau A. Micouin L. Synlett  2006,  2349 
  • 4i Nájera C. Sansano JM. Angew. Chem.  2005,  44:  6272 
  • 4j Husinec S. Savic V. Tetrahedron: Asymmetry  2005,  16:  2047 
  • For recent reviews on asymmetric synthesis of α-amino acids, see:
  • 5a Nájera C. Sansano JM. Chem. Rev.  2007,  107:  4273 
  • 5b Calaza MI. Cativiela C. Eur. J. Org. Chem.  2008,  3427 
  • 6a Chen C. Li X. Schreiber SL. J. Am. Chem. Soc.  2003,  125:  10174 
  • 6b Knöpfel TF. Aschwanden P. Ichikawa T. Watanabe T. Carreira EM. Angew. Chem. Int. Ed.  2004,  43:  5971 
  • 6c Zheng W. Zhou Y.-G. Org. Lett.  2005,  7:  5055 
  • 6d Stohler R. Wahl F. Pfaltz A. Synthesis  2005,  1431 
  • 6e Zheng W. Zhou Y.-G. Tetrahedron Lett.  2007,  48:  4619 
  • 6f Zheng W. Chen G.-Y. Zhou YG. Li Y.-X. J. Am. Chem. Soc.  2007,  129:  750 
  • 6g Nájera C. Retamosa MG. Sansano JM. Angew. Chem. Int. Ed.  2008,  47:  6055 
  • 6h Nájera C. Retamosa MG. Martín-Rodríguez M. Sansano JM. de Cózar A. Cossío FP. Eur. J. Org. Chem.  2009,  5622 
  • 6i Yu SB. Hu X.-P. Deng J. Wang D.-Y. Duan Z.-C. Zheng Z. Tetrahedron: Asymmetry  2009,  20:  621 
  • 7a Nájera C. Retamosa MG. Sansano JM. Org. Lett.  2007,  9:  4025 
  • 7b Nájera C. Retamosa MG. Sansano JM. de Cózar A. Cossío FP. Tetrahedron: Asymmetry  2008,  19:  2913 
  • 8a Gao W. Zhang X. Raghunath M. Org. Lett.  2005,  7:  4241 
  • 8b Cabrera S. Gómez-Arrayás R. Carretero JC. J. Am. Chem. Soc.  2005,  127:  16394 
  • 8c Yan X.-X. Peng Q. Zhang Y. Zhang K. Hong W. Hou X.-L. Wu Y.-D. Angew Chem. Int. Ed.  2006,  45:  1979 
  • 8d Llamas T. Gómez-Arrayás R. Carretero JC. Org. Lett.  2006,  8:  1795 
  • 8e Llamas T. Gómez-Arrayás R. Carretero JC. Synthesis  2007,  950 
  • 8f Shi J.-W. Shi JW. Tetrahedron: Asymmetry  2007,  18:  645 
  • 8g Martín-Matute B. Pereira SI. Peña-Cabrera E. Adrio JA. Silva MS. Carretero JC. Adv. Synth. Catal.  2007,  349:  1714 
  • 8h Cabrera S. Gómez-Arrayás R. Martín-Matute B. Cossío FP. Carretero JC. Tetrahedron  2007,  63:  6587 
  • 8i López-Pérez A. Adrio J. Carretero JC. J. Am. Chem. Soc.  2008,  130:  10084 
  • 8j Fukuzawa S. Oki HZY. Org. Lett.  2008,  10:  1747 
  • 8k Wang C.-J. Liang G. Xue ZY. Gao F.
    J. Am. Chem. Soc.  2008,  130:  17250 
  • 8l Kim HY. Shih H.-J. Knabe WE. Oh K. Angew. Chem. Int. Ed.  2009,  48:  7420 
  • 8m López-Pérez A. Adrio J. Carretero JC. Angew. Chem. Int. Ed.  2009,  48:  340 
  • 8n Hernández-Toribio J. Gómez-Arrayás R. Martín-Matute B. Carretero JC. Org. Lett.  2009,  11:  393 
  • 8o Wang C.-J. Xue ZY. Liang G. Lu Z. Chem. Commun.  2009,  2905 
  • 8p For copper(II)-catalyzed 1,3-dipolar cycloadditions, see: Oderaotoshi Y. Cheng W. Fujitomi S. Kasano Y. Minakata S. Komatsu M. Org. Lett.  2003,  5:  5043 
  • 9a Gothelf AS. Gothelf KV. Hazell RG. Jørgensen KA. Angew. Chem. Int. Ed.  2002,  41:  4236 
  • 9b Dogan O. Koyuncu H. G arner P. Bulut A. Youngs WJ. Panzner M. Org. Lett.  2006,  8:  4687 
  • 10 Shi J.-W. Zhao M.-X. Lei Z.-Y. Shi M. J. Org. Chem.  2008,  73:  305 
  • 11a Saito S. Tsubogo T. Kobayashi S. J. Am. Chem. Soc.  2007,  129:  5364 
  • 11b Tsubogo T. Saito S. Seki K. Yamashita Y. Kobayashi S. J. Am. Chem. Soc.  2008,  130:  13321 
  • The employment of organocatalysts has been reported:
  • 12a Alemparte C. Blay G. Jørgensen KA. Org. Lett.  2005,  7:  4569 
  • 12b Arai S. Takahashi F. Tsuji R. Nishida A. Heterocycles  2006,  67:  495 
  • 12c Ibrahem I. Ríos R. Vesely J. Córdova A. Tetrahedron Lett.  2007,  48:  6252 
  • 12d Xue M.-X. Zhang X.-M. Gong L.-Z. Synlett  2008,  691 
  • 12e Vicario JL. Reboredo S. Badía D. Carrillo L. Angew. Chem. Int. Ed.  2007,  46:  5168 
  • 12f Agbodjan AA. Cooley BE. Copley RCB. Corfield JA. Flanagan RC. Glover BN. Guidetti R. Haigh D. Howes PD. Jackson MM. Matsuoka RT. Medhurst KJ. Millar A. Sharp MJ. Slater MJ. Toczko JF. Xie S. J. Org. Chem.  2008,  73:  3094 
  • 12g Flanagan RC. Xie S. Millar A. Org. Process Res. Dev.  2008,  12:  1307 
  • 12h Nakano M. Terada M. Synlett  2009,  1670 
  • 12i Yu LHeL. Chen X.-H. Song J. Chen W.-J. Gong L.-Z. Org. Lett.  2009,  11:  4946 
  • 12j Chen X.-H. Zhang W.-Q. Gong L.-Z. J. Am. Chem. Soc.  2009,  130:  5652 
  • 12k Chen X.-H. Wei Q. Luo S.-W. Xiao H. Gong L.-Z. J. Am. Chem. Soc.  2009,  130:  13819 
  • 13 For a recent review about Lewis acid vs. organocatalytic asymmetric 1,3-DC, see: Nájera C. Sansano JM. Yus M. J. Braz. Chem. Soc.  2009,  in press
  • 14 Momiyama N. Yamamoto H. J. Am. Chem. Soc.  2004,  126:  5360 
15

The BINAP-AgSbF6 (2:1) chiral cluster was not characterized because it afforded lower endo/exo diastereoselectivity, such as occurred in the previously reported chiral BINAP-AgClO4-catalyzed 1,3-DC (ref. 7).

16

General Procedure for the Catalytic Enantioselective 1,3-DC Using Silver Salts
A solution of the imino ester (1 mmol) and dipolarophile
(1 mmol) in toluene (5 mL) was added to a suspension containing (R)- or (S)-BINAP (0.05 mmol, 31 mg) and silver(I) salt (0.05 mmol) in toluene (5 mL). To the resulting suspension Et3N (0.05 mmol, 7 µL) was added and the mixture stirred at r.t. and in the absence of the light for 16-48 h (see main text). The reaction was filtered, the organic filtrate was directly evaporated, and the residue was purified by recrystallization or by flash chromatography yielding pure endo cycloadducts.
General Procedure for the Three-Component Catalytic Enantioselective 1,3-DC Using Silver Salts
To a suspension containing (R)- or (S)-BINAP (0.05 mmol, 31 mg) and AgSbF6 (0.05 mmol, 17 mg) in toluene (10 mL) was added the freshly distilled aldehyde (1 mmol), glycine methyl ester hydrochloride (1 mmol), the dipolarophile (1 mmol), and Et3N (140 µL, 1.05 mmol). The mixture was stirred at r.t. and in the absence of the light for 16-48 h (see main text). Following the same workup as that described above, final cycloadducts 3aa and 8c were obtained.