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

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

Abstract

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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

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References

References and Notes

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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

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