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

Dieter Enders; Chuan Wang; Jan W. Bats

doi:10.1055/s-0029-1217380

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synlett 2009(11): 1777-1780
DOI: 10.1055/s-0029-1217380

LETTER

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

Dieter Enders*^a, Chuan Wang^a, Jan W. Bats^b
^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

Further Information

Publication History

Received 26 March 2009
Publication Date:
15 June 2009 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

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.

Google Scholar
1b Dalko PI. Enantioselective Organocatalysis Wiley-VCH; Weinheim: 2007.

Google Scholar
1c Special issue on organocatalysis: Chem. Rev. 2007, 107: issue 12

Google Scholar
1d Pellissier H. Tetrahedron 2007, 63: 9267

Google Scholar
1e Dondoni A. Massi A. Angew. Chem. Int. Ed. 2008, 47: 4638 ; Angew. Chem. 2008, 120, 4716

Google Scholar
1f Kotsuki H. Ikishima H. Okuyama A. Heterocycles 2008, 75: 493

Google Scholar
1g Kotsuki H. Ikishima H. Okuyama A. Heterocycles 2008, 75: 757

Google Scholar
1h Enders D. Narine AA. J. Org. Chem. 2008, 73: 7857

Google Scholar
1i Melchiorre P. Marigo M. Carlone A. Bartoli G. Angew. Chem. Int. Ed. 2008, 47: 6138 ; Angew. Chem. 2008, 120, 6232

Google Scholar
For recent reviews on domino reactions, see:
2a Tietze LF. Chem. Rev. 1996, 96: 115

Google Scholar
2b Tietze LF. Brasche G. Gericke K. Domino Reactions in Organic Synthesis Wiley-VCH; Weinheim: 2006.

Google Scholar
2c Pellissier H. Tetrahedron 2006, 62: 1619

Google Scholar
2d Pellissier H. Tetrahedron 2006, 62: 2143

Google Scholar
2e Nicolaou KC. Edmonds DJ. Bulger PG. Angew. Chem. Int. Ed. 2006, 45: 7134 ; Angew. Chem. 2006, 118, 7292

Google Scholar
2f Chapman CJ. Frost CG. Synthesis 2007, 1

Google Scholar
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

Google Scholar
3b Yu X. Wang W. Org. Biomol. Chem. 2008, 6: 2037

Google Scholar
For selected examples of organocatalytic domino reactions, see:
4a Yang JW. Fonseca MTH. List B. J. Am. Chem. Soc. 2005, 127: 15036

Google Scholar
4b Huang Y. Walji AM. Larsen CH. MacMillan DWC. J. Am. Chem. Soc. 2005, 127: 15051

Google Scholar
4c Enders D. Hüttl MRM. Grondal C. Raabe G. Nature 2006, 441: 861

Google Scholar
4d Wang W. Li H. Wang J. Zu L. J. Am. Chem. Soc. 2006, 128: 10354

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

Google Scholar
4f Enders D. Narine AA. Benninghaus TR. Raabe G. Synlett 2007, 1667

Google Scholar
4g Carlone A. Cabrera S. Marigo M. Jørgensen KA. Angew. Chem. Int. Ed. 2007, 46: 1101 ; Angew. Chem. 2007, 119, 1119

Google Scholar
4h Hayashi Y. Okano T. Aratake S. Hazelard D. Angew. Chem. Int. Ed. 2007, 46: 4922 ; Angew. Chem. 2007, 119, 5010

Google Scholar
4i Vicario JL. Reboredo L. Badía D. Carrillo L. Angew. Chem. Int. Ed. 2007, 46: 5168 ; Angew. Chem. 2007, 119, 5260

Google Scholar
4j Rueping M. Sugiono E. Merino E. Angew. Chem. Int. Ed. 2008, 47: 3046 ; Angew. Chem. 2008, 120, 3089

Google Scholar
4k Enders D. Wang C. Bats JW. Angew. Chem. Int. Ed. 2008, 47: 7539 ; Angew. Chem. 2008, 120, 7649

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

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

Google Scholar
4n Enders D. Hüttl MRM. Raabe G. Bats JW. Adv. Synth. Catal. 2008, 350: 267

Google Scholar
4o Kotame P. Hong B.-C. Liao J.-H. Tetrahedron Lett. 2009, 50: 704

Google Scholar
4p Franzén J. Fisher A. Angew. Chem. Int. Ed. 2009, 48: 787 ; Angew. Chem. 2009, 121, 801

Google Scholar
For reviews on organocatalytic Michael additions, see:
5a Tsogoeva SB. Eur. J. Org. Chem. 2007, 1701

Google Scholar
5b Sulzer-Mossé S. Alexakis A. Chem. Commun. 2007, 3123

Google Scholar
5c Vicario JL. Badía D. Carrillo L. Synthesis 2007, 2065

Google Scholar
5d Almaºi D. Alonso DA. Nájera C. Tetrahedron: Asymmetry 2007, 18: 299

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

Google Scholar
6b Corey EJ. Zhang F.-Y. Org. Lett. 2000, 2: 4257

Google Scholar
6c Halland N. Hazell RG. Jørgensen KA. J. Org. Chem. 2002, 67: 8331

Google Scholar
6d Tsogoeva SB. Jagtap SB. Ardemasova ZA. Kalikhevich VN. Eur. J. Org. Chem. 2004, 4014

Google Scholar
6e Vukalya B. Varga S. Csámpai A. Soós T. Org. Lett. 2005, 7: 1967

Google Scholar
6f Mitchell CET. Brenner SE. Ley SV. Chem. Commun. 2005, 5346

Google Scholar
6g Prieto A. Halland N. Jørgensen KA. Org. Lett. 2005, 7: 3897

Google Scholar
6h Ooi T. Takada S. Fujioka S. Maruoka K. Org. Lett. 2005, 7: 5143

Google Scholar
6i Mitchell CET. Brenner SE. García-Fortanet J. Ley SV. Org. Biomol. Chem. 2006, 4: 2039

Google Scholar
6j Hanessian S. Shao Z. Warrier JS. Org. Lett. 2006, 8: 4787

Google Scholar
6k Tsogoeva SB. Jagtap SB. Ardemasova ZA. Tetrahedron: Asymmetry 2006, 17: 989

Google Scholar
6l Gotoh H. Ishikawa H. Hayashi Y. Org. Lett. 2007, 9: 5307

Google Scholar
6m Hojabri L. Hartikka L. Moghaddam FM. Arvidsson PI. Adv. Synth. Catal. 2007, 349: 740

Google Scholar
6n Vakulya B. Varga S. Soós T. J. Org. Chem. 2008, 73: 3475

Google Scholar
6o Li P. Wang Y. Liang X. Ye J. Chem. Commun. 2008, 3302

Google Scholar
6p Zhong S. Chen Y. Petersen JL. Akhmedov NG. Shi X. Angew. Chem. Int. Ed. 2009, 48: 1279 ; Angew. Chem. 2009, 121, 1305

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

Google Scholar
7b Zhao G.-L. Ibrahem I. Dziedzic P. Sun J. Bonneau C. Córdova A. Chem. Eur. J. 2008, 14: 10007

Google Scholar
7c Lv J. Zhang J. Lin Z. Wang Y. Chem. Eur. J. 2009, 15: 972

Google Scholar
7d Zu L. Zhang S. Xie H. Wang W. Org. Lett. 2009, 11: 1627

Google Scholar
8 For a review on organocatalytic aldol reactions, see: Guillena G. Nájera C. Ramón DJ. Tetrahedron: Asymmetry 2007, 18: 2249

Crossref 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

Google Scholar
9b Kriis K. Kanger T. Laars M. Müürisepp A.-M. Pehk T. Lopp M. Synlett 2006, 1699

Google Scholar
9c Enders D. Niemeier O. Straver L. Synlett 2006, 3399

Google Scholar
9d Hayashi Y. Sekiziwa H. Yamaguchi J. Gotoh H. J. Org. Chem. 2007, 72: 6493

Google Scholar
9e Yoshitomi Y. Makino K. Hamada Y. Org. Lett. 2007, 9: 2457

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

Google Scholar
10b Brandau B. Maerten E. Jørgensen KA.
J. Am. Chem. Soc. 2006, 128: 14986

Google Scholar
10c Govender T. Hojbri L. Moghaddam FM. Arvidsson PI. Tetrahedron: Asymmetry 2006, 17: 1763

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

Google Scholar
10e Li H. Wang J. Xie H. Zu L. Jiang W. Duesler EN. Wang W. Org. Lett. 2007, 9: 965

Google Scholar
10f Hong B.-C. Nimje RY. Sadani AA. Liao J.-H. Org. Lett. 2008, 10: 2345

Google Scholar
10g Penon O. Carlone A. Mazzanti A. Locatelli M. Sambri L. Bartoli G. Melchiorre P. Chem. Eur. J. 2008, 14: 4788

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

Google Scholar
11b Mielgo A. Palomo C. Chem. Asian J. 2008, 922

Google Scholar

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.