Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 348, Issue 16-17, Pages 2376-2380Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200600308
Keywords
cycloaddition; cyclopentanes; D-A cyclopropanes; multicomponent reactions; triflic imide; zwitterions
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[3+2] Cycloadditions of silyl enol ethers with donor-acceptor (D-A) cyclopropanes, such as 2-alkoxycyclopropanecarboxylates and 2-(p-methoxyphenyl)cyclopropyl phenyl ketone, proceed in the presence of a catalytic amount of triflic imide (Tf2NH) to give functionalized cyclopentanes in high yield. The catalytic process allows promotion of the cycloaddition of substrates incorporating Lewis basic functions, such as ether and carbamate moieties. Moreover, multicomponent [4+2]-[3+2] cascade cycloadditions of alpha,beta-unsaturated carbonyl compounds, 2-siloxydienes and D-A cyclopropanes to form highly-functionalized bicyclo[4.3.0]nonanes have been demonstrated.
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