Gold(I)-catalyzed synthesis of highly substituted furans

Organic Letters

Volumn 7, Issue 18, 2005, Pages 3925-3927

  Suhre, Michael H ^a   Reif, Michael ^a   Kirsch, Stefan F ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 24944452788     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0514101     Document Type: Article

References (59)

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33. 3 catalyzed the formation of allene 2a less effectively. Generation of furan 3a was not catalyzed.
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48. 3 (2 mol %) did not lead to an increase in the formation of furan 3a.
49. 3)AuCl did not give a catalytically active gold(I) species.
50. 4 274.1205, found 274.1206.
51. With reaction times >3 h, decomposition of product 3n was observed.
52. The origin of this effect remains unclear.
53. Dichloromethane was purchased from Fluka and contained less than 0.005% of water.
54. In the presence of higher amounts of water (10% v/v), furan formation was not observed.
55. Inanaga, J.; Baba, Y.; Hanamoto, T. Chem. Lett. 1993, 241-244.
56. Propargyl vinyl ethers 1b and 1e were obtained as a mixture of E-and Z-isomers. The Z-isomers of 1b and 1e were isolated in 15% and 38% yield, respectively.
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58. 4] led to a quantitative furan formation.
59. Allene 2a was detected as intermediary occurring species in the catalyzed transformation 1a → 3a by capillary gas chromatography.