Regioselective Domino Metathesis of Unsymmetrical 7??Oxanorbornenes with Electron??Rich Vinyl Acetate toward Biologically Active Glutamate Analogues

…, GT Swanson, K Shimamoto, R Sakai

Index: Oikawa, Masato; Ikoma, Minoru; Sasaki, Makoto; Gill, Martin B.; Swanson, Geoffrey T.; Shimamoto, Keiko; Sakai, Ryuichi European Journal of Organic Chemistry, 2009 , # 32 p. 5531 - 5548

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Citation Number: 13

Abstract

Abstract In this article a regioselective domino metathesis reaction of unsymmetrical 7- oxanorbornenes, readily available by a tandem Ugi/Diels–Alder reaction as a key step, promoted by the Hoveyda–Grubbs second-generation catalyst in the presence of electron- rich vinyl acetate as a cross metathesis (CM) substrate is reported. The mechanism for the unusually high regioselectivity observed in the CM reaction was investigated, and a ...