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Gold(I)-Catalyzed Intramolecular Amination of Allylic Alcohols With Alkylamines

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journal contribution
posted on 18.03.2011, 00:00 by Paramita Mukherjee, Ross A. Widenhoefer
A 1:1 mixture of (1)AuCl [1 = P(t-Bu)2o-biphenyl] and AgSbF6 catalyzes the intramolecular amination of allylic alcohols with alkylamines to form substituted pyrrolidine and piperidine derivatives. Gold(I)-catalyzed cyclization of (R,Z)-8-(N-benzylamino)-3-octen-2-ol (96% ee, 95% de) led to isolation of (R,E)-1-benzyl-2-(1-propenyl)piperidine in 99% yield with 96% ee, consistent with the net syn addition of the amine relative to the departing hydroxyl group.

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