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

Journal Article

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.

Full Text

Duke Authors

Cited Authors

  • Mukherjee, P; Widenhoefer, RA

Published Date

  • March 18, 2011

Published In

Volume / Issue

  • 13 / 6

Start / End Page

  • 1334 - 1337

PubMed ID

  • 21314103

Electronic International Standard Serial Number (EISSN)

  • 1523-7052

Digital Object Identifier (DOI)

  • 10.1021/ol103175w

Language

  • eng

Conference Location

  • United States