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Synfacts 2005(2): 0227-0227  
DOI: 10.1055/s-2005-916081
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Pd-Catalyzed Stereospecific Ring-Opening of α,β-Unsaturated-γ,δ-Epoxy Esters

Contributor(s): Mark Lautens, Y. Eric Fang
M. Miyashita*, T. Mizutani, G. Tadano, Y. Iwata, M. Miyazawa, K. Tanino
Hokkaido University, Japan
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Publication History

Publication Date:
25 October 2005 (online)

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Significance

A regioselective and stereospecific azide ring-opening of α,β-unsaturated-γ,δ-epoxy esters was achieved using TMSN3 in the presence of catalytic Pd(PPh3)4. A vicinal hydroxy azide was obtained in excellent yield with retention of ste­reochemistry. When the epoxide was fused with a six-membered ring, the catalyst combination of Pd(OAc)2 (10%) and P(2-furyl)3 was optimal. The ring-opening product was converted into a quaternary γ-amino acid using a few trivial transformations.