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

Publication ,  Journal Article
Mukherjee, P; Widenhoefer, RA
Published in: Organic letters
March 2011

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.

Duke Scholars

Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

March 2011

Volume

13

Issue

6

Start / End Page

1334 / 1337

Related Subject Headings

  • Stereoisomerism
  • Pyrrolidines
  • Propanols
  • Piperidines
  • Organic Chemistry
  • Gold
  • Cyclization
  • Combinatorial Chemistry Techniques
  • Catalysis
  • Amines
 

Citation

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Mukherjee, P., & Widenhoefer, R. A. (2011). Gold(I)-catalyzed intramolecular amination of allylic alcohols with alkylamines. Organic Letters, 13(6), 1334–1337. https://doi.org/10.1021/ol103175w
Mukherjee, Paramita, and Ross A. Widenhoefer. “Gold(I)-catalyzed intramolecular amination of allylic alcohols with alkylamines.Organic Letters 13, no. 6 (March 2011): 1334–37. https://doi.org/10.1021/ol103175w.
Mukherjee P, Widenhoefer RA. Gold(I)-catalyzed intramolecular amination of allylic alcohols with alkylamines. Organic letters. 2011 Mar;13(6):1334–7.
Mukherjee, Paramita, and Ross A. Widenhoefer. “Gold(I)-catalyzed intramolecular amination of allylic alcohols with alkylamines.Organic Letters, vol. 13, no. 6, Mar. 2011, pp. 1334–37. Epmc, doi:10.1021/ol103175w.
Mukherjee P, Widenhoefer RA. Gold(I)-catalyzed intramolecular amination of allylic alcohols with alkylamines. Organic letters. 2011 Mar;13(6):1334–1337.
Journal cover image

Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

March 2011

Volume

13

Issue

6

Start / End Page

1334 / 1337

Related Subject Headings

  • Stereoisomerism
  • Pyrrolidines
  • Propanols
  • Piperidines
  • Organic Chemistry
  • Gold
  • Cyclization
  • Combinatorial Chemistry Techniques
  • Catalysis
  • Amines