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Synlett 2016; 27(04): 571-574
DOI: 10.1055/s-0035-1561279
DOI: 10.1055/s-0035-1561279
cluster
Direct Asymmetric Friedel–Crafts Reaction of Naphthols with Acetals Catalyzed by Chiral Brønsted Acids
Further Information
Publication History
Received: 01 September 2015
Accepted after revision: 14 November 2015
Publication Date:
23 December 2015 (online)
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 organocatalysisSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561279.
- Supporting Information
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Reference and Notes
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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).