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1,3-Dipolar cycloaddition of unstabilised azomethine ylides by Lewis base catalysis

✍ Scribed by Pandiancherri, Shveta; Ryan, Sarah J.; Lupton, David W.

Book ID
118018654
Publisher
Royal Society of Chemistry
Year
2012
Tongue
English
Weight
635 KB
Volume
10
Category
Article
ISSN
1477-0520

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✦ Synopsis

Lewis base catalysed 1,3-dipolar cycloaddition between Ξ±,Ξ²-unsaturated acyl fluorides and N-[(trimethylsilyl)methyl]amino ethers has been achieved using 1 mol% DMAP. Competition experiments and (19)F-NMR studies indicate that the cycloaddition occurs preferentially between the Ξ±,Ξ²-unsaturated acyl fluoride and the unstabilised azomethine ylide. In addition, an enantioselective variant, using chiral isothiourea catalysts, has been achieved with 14% ee.

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## Abstract Azomethine ylides generated from 5‐(alkoxycarbonylmethyl)phenanthridinium cations were studied in 1,3‐dipolar cycloadditions with dimethyl maleate and dimethyl fumarate as dipolarophiles. The cycloadducts with the pyrrolidino[1,2‐f]phenanthridine skeleton easily underwent dehydrogenatio