4.7 Article

Highly diastereroselective synthesis of dihydrofurans and dihydropyrroles via pyridine catalyzed formal [4+1] annulation

Journal

CHEMICAL COMMUNICATIONS
Volume 47, Issue 4, Pages 1342-1344

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c0cc02347g

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Funding

  1. Natural Sciences Foundation of China [20821002, 20932008]
  2. Major State Basic Research Development Program [2009CB825300]
  3. Chinese Academy of Sciences

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A pyridine-catalyzed ylide cyclization affording dihydrofurans and dihydropyrroles has been developed. In the presence of a catalytic amount of pyridine and Fe(Tcpp)Cl, alpha-ylidene-beta-diketones and alpha, beta-unsaturated imines react with diazoacetates providing dihydrofurans and dihydropyrroles respectively, in up to 96% yield with high diastereoselectivities.

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