Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 354, Issue 18, Pages 3545-3550Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201200375
Keywords
a-acylketene dithioacetals; [3+2]?cycloaddition; propargylamines; pyrroles; synthetic methods
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Funding
- National Natural Sciences Foundation of China [20972026, 21172032]
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A new [3+2]?cycloaddition strategy for the direct synthesis of highly substituted pyrroles from the readily available a-acylketene dithioacetals (or related substrates) and commercially available propargylamines under mild metal-free conditions has been developed. In this reaction, the acyl group plays a critical role in driving the conjugate addition of propargylamine and further cyclization to give pyrroles. Furthermore, the wide scope was confirmed by the preparation of 1,2,3,4-tetrasubstituted pyrroles (6070% yields) via a formal 1,2-acyl migrating [3+2]?cycloaddition pathway with N-methylprop-2-yn-1-amine as the secondary amine component.
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