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Synfacts 2005(0): 0047-0047  
DOI: 10.1055/s-2005-869937
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Hydroxylamines as Oxygen-Based Nucleo­-philes in Allylic Substitution Reaction

Contributor(s): Mark Lautens, Y. Eric Fang
H. Miyabe, K. Yoshida, M. Yamauchi, Y. Takemoto*
Kyoto University, Japan
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Publikationsdatum:
20. Juli 2005 (online)

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Significance

Transition-metal-catalyzed allylation with oxygen-based nucleophiles are not well developed due to their low nucleophilicity and poor regioselectivity. Hydroxylamines were shown to give better yields and regioselectivity in both Pd- and Ir-catalyzed O-allylic substitution reactions due to their higher nucleophilicity. In the case of Ir-catalyzed reactions, good enantiomeric excess was obtained using a chiral Ph-pybox ligand.