Exploiting Grubbs Catalysts with Novel Reactivity

By: William Sommer, Aldrich ChemFiles 2009, 9.6, 7.

Aldrich ChemFiles 2009, 9.6, 7.

The Howell group recently reported the first synthesis of tetrasubstituted olefins using cross metathesis during the course of investigating the synthesis of a-alkylidene-ß-lactams, which serve as building blocks for the preparation of ß-lactam antibiotics. The Hoveyda-Grubbs catalyst (2nd Generation) outperformed the Grubbs catalyst (2nd Generation) in cross metathesis and portion-wise catalyst addition led to increased product yields.1 Using variable catalyst loadings, the desired tetrasubstituted olefin was generated in good yields (Scheme 3).

Scheme 3

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  1. Liang, Y.et al. Tetrahedron Lett. 2009, 50, 1020.

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