Gold(I)-Catalyzed Amination of Allylic Alcohols with Cyclic Ureas and Related Nucleophiles

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2010

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Abstract

A 1:1 mixture of [P(t-Bu)(2)-o-biphenyl]AuCl and AgSbF6 catalyzes the Intermolecular amination of allylic alcohols with 1-methylimidazolidin-2-one and related nucleophiles that, in the case of gamma-unsubstituted or gamma-methyl-substituted allylic alcohols, occurs with high gamma-regloselectivity and syn-stereoselectivity.

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catalyzed direct amination, titanium(iv) isopropoxide, neutral, conditions, secondary-amines, palladium, allylation, complexes, efficient, alkylation, ligands, chemistry, organic

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Mukherjee,Paramita;Widenhoefer,Ross A.. 2010. Gold(I)-Catalyzed Amination of Allylic Alcohols with Cyclic Ureas and Related Nucleophiles. Organic letters 12(6): 1184-1187.

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https://hdl.handle.net/10161/4110

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10.1021/ol902923e

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Widenhoefer

Ross A. Widenhoefer

Professor of Chemistry

Research in the Widenhoefer group is directed toward the development and mechanistic analysis of new organotransition metal-catalyzed transformations for application in the synthesis of functionalized organic molecules. In particular, our group has a long-standing interest in the functionalization of C–C multiple bonds with carbon and heteroatom nucleophiles catalyzed by electrophilic late transition metal complexes, with a recent focus on the synthetic and mechanistic aspect of gold(I) pi-activation catalysis. Current areas of inquiry include the following:

  1. Gold(I) and Pt(II)-catalyzed hydroamination of alkenes an allenes.
  2. Gold(I)-catalyzed dehydrative amination of underivatized allylic alcohols.
  3. Synthesis and study of cationic, two-coordinate gold pi-complexes.
  4. Evaluating the role of bis(gold) complexes in gold pi-activation catalysis.

More detailed descriptions of these research projects can be found at our group web page.

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