PDF herunterladen
Synlett 2009(11): 1777-1780  
DOI: 10.1055/s-0029-1217380
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Synthesis of Functionalized 3,4-Dihydronaphthalenes via an Organocatalytic Domino Nitroalkane-Michael/Aldol Condensation Reaction

Dieter Enders*a, Chuan Wanga, Jan W. Batsb
a Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
Fax: +49(241)8092127; e-Mail: enders@rwth-aachen.de;
b Institute of Organic Chemistry and Chemical Biology, University Frankfurt, Marie-Curie-Str. 11, 60439 Frankfurt am Main, Germany
Weitere Informationen

Publikationsverlauf

Received 26 March 2009
Publikationsdatum:
15. Juni 2009 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik
Preview

Abstract

An organocatalytic domino nitroalkane-Michael addition/aldol condensation reaction has been developed. This process provides an efficient asymmetric synthesis of trisubstituted 3,4-dihydronaphthalenes in moderate to good yields (40-75%) and high stereoselectivities (de >98%, ee = 91 to >99%).

Key words

dihydronaphthalenes - organocatalysis - domino reaction - Michael addition - aldol condensation

    References and Notes

  • For recent reviews on organocatalysis, see:
  • 1a Berkessel A. Gröger H. Asymmetric Organocatalysis   Wiley-VCH; Weinheim: 2005. 
  • 1b Dalko PI. Enantioselective Organocatalysis   Wiley-VCH; Weinheim: 2007. 
  • 1c Special issue on organocatalysis: Chem. Rev.  2007,  107:  issue 12 
  • 1d Pellissier H. Tetrahedron  2007,  63:  9267 
    Suche in Google Scholar
  • 1e Dondoni A. Massi A. Angew. Chem. Int. Ed.  2008,  47:  4638 ; Angew. Chem. 2008, 120, 4716
    Suche in Google Scholar
  • 1f Kotsuki H. Ikishima H. Okuyama A. Heterocycles  2008,  75:  493 
    Suche in Google Scholar
  • 1g Kotsuki H. Ikishima H. Okuyama A. Heterocycles  2008,  75:  757 
    Suche in Google Scholar
  • 1h Enders D. Narine AA. J. Org. Chem.  2008,  73:  7857 
    Suche in Google Scholar
  • 1i Melchiorre P. Marigo M. Carlone A. Bartoli G. Angew. Chem. Int. Ed.  2008,  47:  6138 ; Angew. Chem. 2008, 120, 6232
    Suche in Google Scholar
  • For recent reviews on domino reactions, see:
  • 2a Tietze LF. Chem. Rev.  1996,  96:  115 
    Suche in Google Scholar
  • 2b Tietze LF. Brasche G. Gericke K. Domino Reactions in Organic Synthesis   Wiley-VCH; Weinheim: 2006. 
  • 2c Pellissier H. Tetrahedron  2006,  62:  1619 
    Suche in Google Scholar
  • 2d Pellissier H. Tetrahedron  2006,  62:  2143 
    Suche in Google Scholar
  • 2e Nicolaou KC. Edmonds DJ. Bulger PG. Angew. Chem. Int. Ed.  2006,  45:  7134 ; Angew. Chem. 2006, 118, 7292
    Suche in Google Scholar
  • 2f Chapman CJ. Frost CG. Synthesis  2007,  1 
  • For reviews on organocatalytic domino reactions, see:
  • 3a Enders D. Grondal C. Hüttl MRM. Angew. Chem. Int. Ed.  2007,  46:  1570 ; Angew. Chem. 2007, 119, 1590
    Suche in Google Scholar
  • 3b Yu X. Wang W. Org. Biomol. Chem.  2008,  6:  2037 
    Suche in Google Scholar
  • For selected examples of organocatalytic domino reactions, see:
  • 4a Yang JW. Fonseca MTH. List B. J. Am. Chem. Soc.  2005,  127:  15036 
    Suche in Google Scholar
  • 4b Huang Y. Walji AM. Larsen CH. MacMillan DWC. J. Am. Chem. Soc.  2005,  127:  15051 
    Suche in Google Scholar
  • 4c Enders D. Hüttl MRM. Grondal C. Raabe G. Nature  2006,  441:  861 
    Suche in Google Scholar
  • 4d Wang W. Li H. Wang J. Zu L. J. Am. Chem. Soc.  2006,  128:  10354 
    Suche in Google Scholar
  • 4e Enders D. Hüttl MRM. Runsink J. Raabe G. Wendt B. Angew. Chem. Int. Ed.  2007,  46:  467 ; Angew. Chem. 2007, 119, 471
    Suche in Google Scholar
  • 4f Enders D. Narine AA. Benninghaus TR. Raabe G. Synlett  2007,  1667 
  • 4g Carlone A. Cabrera S. Marigo M. Jørgensen KA. Angew. Chem. Int. Ed.  2007,  46:  1101 ; Angew. Chem. 2007, 119, 1119
    Suche in Google Scholar
  • 4h Hayashi Y. Okano T. Aratake S. Hazelard D. Angew. Chem. Int. Ed.  2007,  46:  4922 ; Angew. Chem. 2007, 119, 5010
    Suche in Google Scholar
  • 4i Vicario JL. Reboredo L. Badía D. Carrillo L. Angew. Chem. Int. Ed.  2007,  46:  5168 ; Angew. Chem. 2007, 119, 5260
    Suche in Google Scholar
  • 4j Rueping M. Sugiono E. Merino E. Angew. Chem. Int. Ed.  2008,  47:  3046 ; Angew. Chem. 2008, 120, 3089
    Suche in Google Scholar
  • 4k Enders D. Wang C. Bats JW. Angew. Chem. Int. Ed.  2008,  47:  7539 ; Angew. Chem. 2008, 120, 7649
    Suche in Google Scholar
  • 4l Zhao G.-L. Rios R. Vesley J. Eriksson L. Córdova A. Angew. Chem. Int. Ed.  2008,  47:  8468 ; Angew. Chem. 2008, 120, 8596
    Suche in Google Scholar
  • 4m Lu M. Zhu D. Lu Y. Hou Y. Tan B. Zhong G. Angew. Chem. Int. Ed.  2008,  47:  10187 ; Angew. Chem. 2008, 120, 10341
    Suche in Google Scholar
  • 4n Enders D. Hüttl MRM. Raabe G. Bats JW. Adv. Synth. Catal.  2008,  350:  267 
    Suche in Google Scholar
  • 4o Kotame P. Hong B.-C. Liao J.-H. Tetrahedron Lett.  2009,  50:  704 
    Suche in Google Scholar
  • 4p Franzén J. Fisher A. Angew. Chem. Int. Ed.  2009,  48:  787 ; Angew. Chem. 2009, 121, 801
    Suche in Google Scholar
  • For reviews on organocatalytic Michael additions, see:
  • 5a Tsogoeva SB. Eur. J. Org. Chem.  2007,  1701 
  • 5b Sulzer-Mossé S. Alexakis A. Chem. Commun.  2007,  3123 
  • 5c Vicario JL. Badía D. Carrillo L. Synthesis  2007,  2065 
  • 5d Almaºi D. Alonso DA. Nájera C. Tetrahedron: Asymmetry  2007,  18:  299 
    Suche in Google Scholar
  • For selected examples of organocatalytic nitroalkane-Michael additions with enals or enones as electrophile, see:
  • 6a Hanessian S. Pham V. Org. Lett.  2000,  2:  2975 
    Suche in Google Scholar
  • 6b Corey EJ. Zhang F.-Y. Org. Lett.  2000,  2:  4257 
    Suche in Google Scholar
  • 6c Halland N. Hazell RG. Jørgensen KA. J. Org. Chem.  2002,  67:  8331 
    Suche in Google Scholar
  • 6d Tsogoeva SB. Jagtap SB. Ardemasova ZA. Kalikhevich VN. Eur. J. Org. Chem.  2004,  4014 
  • 6e Vukalya B. Varga S. Csámpai A. Soós T. Org. Lett.  2005,  7:  1967 
    Suche in Google Scholar
  • 6f Mitchell CET. Brenner SE. Ley SV. Chem. Commun.  2005,  5346 
  • 6g Prieto A. Halland N. Jørgensen KA. Org. Lett.  2005,  7:  3897 
    Suche in Google Scholar
  • 6h Ooi T. Takada S. Fujioka S. Maruoka K. Org. Lett.  2005,  7:  5143 
    Suche in Google Scholar
  • 6i Mitchell CET. Brenner SE. García-Fortanet J. Ley SV. Org. Biomol. Chem.  2006,  4:  2039 
    Suche in Google Scholar
  • 6j Hanessian S. Shao Z. Warrier JS. Org. Lett.  2006,  8:  4787 
    Suche in Google Scholar
  • 6k Tsogoeva SB. Jagtap SB. Ardemasova ZA. Tetrahedron: Asymmetry  2006,  17:  989 
    Suche in Google Scholar
  • 6l Gotoh H. Ishikawa H. Hayashi Y. Org. Lett.  2007,  9:  5307 
    Suche in Google Scholar
  • 6m Hojabri L. Hartikka L. Moghaddam FM. Arvidsson PI. Adv. Synth. Catal.  2007,  349:  740 
    Suche in Google Scholar
  • 6n Vakulya B. Varga S. Soós T. J. Org. Chem.  2008,  73:  3475 
    Suche in Google Scholar
  • 6o Li P. Wang Y. Liang X. Ye J. Chem. Commun.  2008,  3302 
  • 6p Zhong S. Chen Y. Petersen JL. Akhmedov NG. Shi X. Angew. Chem. Int. Ed.  2009,  48:  1279 ; Angew. Chem. 2009, 121, 1305
    Suche in Google Scholar
  • For selected examples of organocatalytic domino reactions involving nitroalkane-Michael additions with enals or enones as electrophiles, see refs 4c, 4e, 4g, 4n, 4o, and:
  • 7a Reyes E. Jiang H. Milelli A. Elsner P. Hazell RG. Jørgensen KA. Angew. Chem. Int. Ed.  2007,  46:  9202 ; Angew. Chem. 2007, 119, 9362
    Suche in Google Scholar
  • 7b Zhao G.-L. Ibrahem I. Dziedzic P. Sun J. Bonneau C. Córdova A. Chem. Eur. J.  2008,  14:  10007 
    Suche in Google Scholar
  • 7c Lv J. Zhang J. Lin Z. Wang Y. Chem. Eur. J.  2009,  15:  972 
    Suche in Google Scholar
  • 7d Zu L. Zhang S. Xie H. Wang W. Org. Lett.  2009,  11:  1627 
    Suche in Google Scholar
  • 8 For a review on organocatalytic aldol reactions, see: Guillena G. Nájera C. Ramón DJ. Tetrahedron: Asymmetry  2007,  18:  2249 
    CrossrefSuche in Google Scholar
  • For selected examples of organocatalytic intramolecular aldol reactions, see:
  • 9a Pidathala C. Hoang L. Vignola N. List B. Angew. Chem. Int. Ed.  2003,  42:  2785 ; Angew. Chem. 2003, 115, 2891
    Suche in Google Scholar
  • 9b Kriis K. Kanger T. Laars M. Müürisepp A.-M. Pehk T. Lopp M. Synlett  2006,  1699 
  • 9c Enders D. Niemeier O. Straver L. Synlett  2006,  3399 
  • 9d Hayashi Y. Sekiziwa H. Yamaguchi J. Gotoh H. J. Org. Chem.  2007,  72:  6493 
    Suche in Google Scholar
  • 9e Yoshitomi Y. Makino K. Hamada Y. Org. Lett.  2007,  9:  2457 
    Suche in Google Scholar
  • For selected examples of organocatalytic domino reactions involving intramolecular aldol reactions, see refs 4c-g, 4n, 4o and:
  • 10a Halland N. Abruel PS. Jørgensen KA. Angew. Chem. Int. Ed.  2004,  43:  1272 ; Angew. Chem. 2004, 116, 1292
    Suche in Google Scholar
  • 10b Brandau B. Maerten E. Jørgensen KA.
    J. Am. Chem. Soc.  2006,  128:  14986 
    Suche in Google Scholar
  • 10c Govender T. Hojbri L. Moghaddam FM. Arvidsson PI. Tetrahedron: Asymmetry  2006,  17:  1763 
    Suche in Google Scholar
  • 10d Wang J. Li H. Xie H. Zu L. Shen X. Wang W. Angew. Chem. Int. Ed.  2007,  46:  9050 ; Angew. Chem. 2007, 119, 9208
    Suche in Google Scholar
  • 10e Li H. Wang J. Xie H. Zu L. Jiang W. Duesler EN. Wang W. Org. Lett.  2007,  9:  965 
    Suche in Google Scholar
  • 10f Hong B.-C. Nimje RY. Sadani AA. Liao J.-H. Org. Lett.  2008,  10:  2345 
    Suche in Google Scholar
  • 10g Penon O. Carlone A. Mazzanti A. Locatelli M. Sambri L. Bartoli G. Melchiorre P. Chem. Eur. J.  2008,  14:  4788 
    Suche in Google Scholar
  • For reviews on diphenylprolinol TMS-ether, see:
  • 11a Palomo C. Mielgo A. Angew. Chem. Int. Ed.  2006,  45:  7876 ; Angew. Chem. 2006, 118, 8042
    Suche in Google Scholar
  • 11b Mielgo A. Palomo C. Chem. Asian J.  2008,  922 
12

Compound 3c: CCDC-725063 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallo-graphic Data Centre via www.ccdc.cam.ac.uk/data_request/cif

13

General Procedure: To a solution of 2-(nitromethyl)-benzaldehyde (1; 1.0 mmol) and α,β-unsatured aldehyde 2 (1.1 mmol, 1.1 equiv) in Et2O (2 mL), was added (S)-di-phenylprolinol TMS-ether [(S)-4; 0.05 mmol, 5 mol%]. The reaction mixture was stirred at the temperature and for the time displayed in Table  [²] .
Workup A: Direct purification of the reaction mixture by flash chromatography afforded 3,4-dihydronaphthalenes 3 (pentane-Et2O, 2-10:1).
Workup B: Direct suction through a funnel followed by washing with Et2O afforded 3c.
Workup C: The reaction mixture was suctioned through a funnel and washed with Et2O. Purification of the obtained solid by flash chromatography (silica gel, pentane-Et2O, 1:3) afforded 3d.
(3 R ,4 S )-3-(2-Methoxyphenyl)-4-nitro-3,4-dihydro-naphthalene-2-carbaldehyde (3c; Figure 2): Isolated as a colorless solid (206 mg, 67%). The ee (>99%) was determined by HPLC on a chiral stationary phase [Chiralcel OD; n-heptane-i-PrOH (8:2); 1.0 mL/min, t R  = 9.04 min(major), 10.29 min (minor, based on the racemic mixture)]; mp 182 ˚C; [α]D ²0 -482 (c 1.0, CHCl3); IR (KBr): 3310 (w), 3000 (w), 2946 (w), 2823 (m), 2728 (w), 2324 (w), 2268 (w), 2184 (w), 2048 (w), 1989 (w), 1942 (w), 1735 (w), 1701 (w), 1663 (vs), 1627 (s), 1599 (m), 1570 (m), 1538 (vs), 1489 (s), 1460 (s), 1435 (m), 1399 (s), 1358 (s), 1327 (m), 1289 (s), 1273 (s), 1245 (vs), 1192 (w), 1158 (vs), 1105 (s), 1052 (s), 1028 (s), 961 (w), 924 (s), 855 (m), 819 (m), 755 (vs), 704 (s) cm-¹; ¹H NMR (400 MHz, CDCl3): δ = 3.95 (s, 3 H, OCH3), 5.48 (br s, J = <2 Hz, 1 H, H-3), 5.62 (br s, J = <2 Hz, 1 H, H-4), 6.60 (dd, J = 7.6, 1.6 Hz, 1 H, H-6′), 6.65 (td, J = 7.6, 0.8 Hz, 1 H, H-5′), 6.91 (d, J = 7.6 Hz, 1 H, H-3′), 7.19 (td, J = 7.6, 1.6 Hz, 1 H, H-4′), 7.36-7.42 (m, 2 H, H-5,7), 7.48-7.54 (m, 2 H, H-6,8), 7.68 (s, 1 H, H-1), 9.73 (s, 1 H, CHO); ¹³C NMR (101 MHz, CDCl3): δ = 34.5 (C-3), 55.6 (OCH3), 86.4 (C-4), 110.8 (C-3′), 120.3 (C-5′), 122.5 (C-1′), 126.9 (C-6′), 128.0 (C-9), 129.0 (C-4′), 129.4 (C-8), 130.9 (C-6), 131.3 (C-5), 131.6 (C-7), 131.7 (C-10), 137.8 (C-2), 144.1 (C-1), 156.7 (C-2′), 190.7 (CHO); MS (EI, 70 eV): m/z (%) = 309.4 (5.8) [M+], 277.3 (2.2), 263.3 (74), 245.3 (50), 235.4 (100), 231.4 (24), 202.3 (65), 189.3 (19), 176.3 (2.7), 165.3 (8.8), 155.3 (7.5), 152.3 (2.7), 127.3 (9.5), 117.6 (9.1), 101.3 (19), 94.8 (7.2), 83.1 (4.7), 77.4 (10), 57.4 (2.2), 51.4 (4.0), 43.3 (2.2); Anal. Calcd for C18H15NO4: C, 69.89; H, 4.89; N, 4.53. Found: C, 69.92; H, 4.94; N, 4.50.

Figure 2