Cross-metathesis of allyl halides with olefins bearing amide and ester groups

Author: Yun, J.I.; Kim, H.R.; Kim, S.K.; Kim, D.; Lee, J.

Description: An investigation was conducted to determine whether the cross-metathesis (CM) of allyl halides tolerates amide groups. The results show that the ruthenium-based complexes I–III serve as poor catalysts for the CM of allyl halides with olefins that contain an N,N-dimethylamide group. In contrast, the Grubbs–Hoveyda–Blechert second generation catalyst (III) efficiently promotes these processes with olefins bearing a Weinreb amide group. Lastly, a reinvestigation of the ester group tolerance of the allyl halide CM with unsaturated esters demonstrated that III serves as an efficient catalyst for these reactions.

Subject headings: Cross-metathesis; Allyl halide; Weinreb amide; Grubbs–Hoveyda–Blechert second generation catalyst

Publication year: 2012

Journal or book title: Tetrahedron

Volume: 68

Issue: 4

Pages: 1177-1184

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Type: Journal Article

Serial number: 690