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Synlett 2015; 26(12): 1720-1724
DOI: 10.1055/s-0034-1380723
DOI: 10.1055/s-0034-1380723
letter
Lewis Acid Catalyzed [3+2] Coupling of Quinone Monoacetals or Quinone Imine Ketals with Vinylcarbamates
Further Information
Publication History
Received: 10 February 2015
Accepted after revision: 09 April 2015
Publication Date:
21 May 2015 (online)
![](https://www.thieme-connect.de/media/synlett/201512/lookinside/thumbnails/st-2015-w0092-l_10-1055_s-0034-1380723-1.jpg)
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-indolinesSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380723.
- Supporting Information
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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.
For reviews, see:
For some recent examples, see:
For reviews, see:
For some recent examples, see:
For coupling of quinone derivatives with alkene nucleophiles, see:
For reviews, see:
For some recent examples, see:
For some recent examples of on formal [3+2] cycloadditions or [3+2] annulations, see: