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Gold(I)-catalyzed intramolecular amination of allylic alcohols with alkylamines.

ABSTRACT: A 1:1 mixture of (1)AuCl [1 = P(t-Bu)(2)o-biphenyl] and AgSbF(6) 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.

SUBMITTER: Mukherjee P

PROVIDER: S-EPMC3429346 | biostudies-literature | 2011 Mar

REPOSITORIES: biostudies-literature

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Gold(I)-catalyzed intramolecular amination of allylic alcohols with alkylamines.

Mukherjee Paramita P Widenhoefer Ross A RA

Organic letters 20110211 6

A 1:1 mixture of (1)AuCl [1 = P(t-Bu)(2)o-biphenyl] and AgSbF(6) 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. ...[more]

PMID: 21314103

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