Direct Asymmetric Friedel–Crafts Reaction of Naphthols with Acetals Catalyzed by Chiral Brønsted Acids

Abstract

The Friedel–Crafts method synthesis of chiral ethers from various acetals and naphthols catalyzed by chiral Brønsted acids with acetic acid as an effective additive is described. We found that the chiral phosphoric acid (R)-TRIP could efficiently catalyze the asymmetric Friedel–Crafts reaction of naphthols with acetals affording chiral ethers in good enantioselectivity and yield.

Key words

Friedel–Crafts reaction - chiral ethers - acetals - chiral Brønsted acid - asymmetric organocatalysis

• Reference and Notes

• 1 L.Q. and P.W. contributed equally.
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• 16 General Catalytic Enantioselective Reaction of the Naphthol with Acetals: Into a 5-mL dry round bottom flask containing a magnetic stirring bar were added the catalyst (0.04 mmol) and the naphthol (0.4 mmol) under argon. Anhydrous 1,2-dichloroethane (1 mL), acetals (0.2 mmol) and AcOH (0.04 mmol) were added sequentially at r.t. The reaction mixture was stirred at 35 °C until the reaction was complete (checked by TLC). Then the reaction was cooled to 0 °C and a few drops of sat. NaHCO₃ were added to quench the reaction. After extraction with CH₂Cl₂ (3 × 2 mL), the combined organic phases were dried with anhyd Na₂SO₄ and concentrated under vacuum to give the crude product. Finally purification by column chromatography afforded the expected chiral ethers.1-[Methoxy(o-tolyl)methyl]naphthalen-2-ol (4b): white crystal; mp 85–87 °C; [α]_D ²⁰ +23 (c 1.0, CHCl₃). ¹H NMR (400 MHz, CDCl₃): δ = 2.65 (s, 3 H), 3.60 (s, 3 H), 6.35 (s, 1 H), 6.88–6.90 (d, J = 6.0 Hz, 1 H), 6.97–7.01 (m, 1 H), 7.18–7.35 (m, 5 H), 7.41–7.43 (m, 1 H), 7.78–7.81 (m, 2 H), 9.23 (s, 1 H). ¹³C NMR (100 MHz, CDCl₃): δ = 19.3, 58.2, 81.6, 119.4, 121.1, 123.0, 126.3, 126.8, 127.8, 128.8, 128.9, 130.3, 130.8, 154.9. HRMS (ESI, +ve): m/z [M – H] calcd for C₁₉H₁₇O₂: 277.1234; found: 277.1228. ee = 55%, determined by chiral HPLC with an OD-H column (hexane–i-PrOH, 99:1); flow rate = 1.0 mL/min; t _R = 7.26 (major), t _R = 8.97 (minor).2-[Methoxy(phenyl)methyl]naphthalen-1-ol (4n): yellow oil; [α]_D ²⁰ +3 (c 1.0, CHCl₃). ¹H NMR (400 MHz, CDCl₃): δ = 3.52 (s, 3 H), 5.57 (s, 1 H), 6.96–6.98 (d, J = 8.4 Hz, 1 H), 7.28–7.38 (m, 6 H), 7.46–7.47 (m, 2 H), 7.73–7.75 (m, 1 H), 8.29–8.31 (m, 1 H), 9.04 (s, 1 H). ¹³C NMR (100 MHz, CDCl₃): δ = 57.4, 87.6, 119.2, 122.3, 125.2, 125.4, 126.2, 126.4, 127.2, 127.4, 128.3, 128.6, 134.0, 140.0, 150.9. ee = 20%, determined by chiral HPLC with an OD-H column (hexane–i-PrOH, 99:1); flow rate: 1.0 mL/min; t _R = 8.70 (major), t _R = 12.30 (minor).