American Chemical Society
ol303128s_si_002.cif (24.15 kB)

Dual Amine and Palladium Catalysis in Diastereo- and Enantioselective Allene Carbocyclization Reactions

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posted on 2012-12-21, 00:00 authored by Meiling Li, Swarup Datta, David M. Barber, Darren J. Dixon
A pyrrolidine and Pd catalyzed diastereoselective carbocyclization of aldehyde and ketone-linked allenes has been developed. The cooperative organo/metal-catalyzed cyclization reaction, which presumably proceeds via an enamine intermediate, is efficient and broad in scope. Also, it has been extended to a catalytic asymmetric variant using diarylprolinol-based organocatalysts to afford substituted cyclopentane and pyrrolidine reaction products in up to 82% ee.