Lewis Acid Catalyzed [3+2] Coupling of Quinone Monoacetals or Quinone Imine Ketals with Vinylcarbamates

Abstract

A mild and concise [3+2] coupling of quinone monoacetals or quinone imine ketals with vinylcarbamates promoted by Lewis acid was realized. Various 2-carbamate-2,3-dihydrobenzofurans and 2-carbamate-indolines have been prepared in moderate to good yields.

Key words

[3+2] coupling - Lewis acid - synthesis - 2-carbamate-2,3-dihydrobenzofurans - 2-carbamate-indolines

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• 8 General Experimental Procedure for the [3+2] Coupling of Quinone Monoacetals or Quinone Imine Ketals 1 with Vinylcarbamates 2 Quinone monoacetal or quinone imine ketal 1 (0.30 mmol) and vinylcarbamate 2 (0.20 mmol) were added to a flame-dried vial equipped with a magnetic stirring bar. Then MeCN (2 mL) was added to dissolve the mixture. Afterwards Cu(OTf)₂ (10.8 mg, 0.02 mmol) was introduced in the solution. The reaction mixture was stirred at 25 °C for 12 h. Then the solvent was evaporated, and the residue was subjected to chromatography (silica gel; hexane–EtOAc, 20:1 to 10:1) to afford the desired product 3.
• 9 Benzyl (5-Methoxy-2,3-dihydrobenzofuran-2-yl)carbamate (3a) Yield 84%, 0.050 g; white solid. ¹H NMR (300 MHz, CDCl₃): δ = 7.26–7.35 (m, 5 H), 6.65–6.74 (m, 3 H), 6.26 (br s, 1 H), 5.75 (d, J = 8.8 Hz, 1 H), 5.08–5.18 (m, 2 H), 3.74 (s, 3 H), 3.49 (dd, J ₁ = 8.3 Hz, J ₂ = 16.4 Hz, 1 H), 2.89 (dd, J ₁ = 16.5 Hz, J ₂ = 4.5 Hz, 1 H). ¹³C NMR (75 MHz, CDCl₃): δ = 155.3, 154.3, 151.8, 135.8, 128.5, 128.3, 128.2, 125.2, 113.3, 110.9, 109.8, 85.3, 67.2, 55.9, 36.1. ESI-HRMS: m/z calcd for C₁₇H₁₇NO₄Na⁺ [M + Na]⁺: 322.1047; found: 322.1055.