Cross-metathesis of allyl halides with olefins bearing an α-alkoxy amide group

Yun, Jeong In; Kim, Deukjoon; Lee, Jongkook

doi:10.1016/j.tetlet.2011.02.043

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Cross-metathesis of allyl halides with olefins bearing an α-alkoxy amide group

Yun, Jeong In;
Kim, Deukjoon;
Lee, Jongkook

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WEB OF SCIENCE

6

Citations

SCOPUS

7

초록

We have examined whether the allyl halide cross-metathesis reaction tolerates alpha-alkoxy amide groups. Ruthenium-based catalysts I-Ill did not catalyze the cross-metathesis of allyl halides in the presence of an alpha-alkoxy N,N-dimethylamide group to any appreciable extent, but the reaction could tolerate either a bulky N,N-diisopropylamide or Weinreb amide group. In particular, the Grubbs-Hoveyda-Blechert 2nd generation catalyst (III) efficiently catalyzed the cross-metathesis of allyl halides with olefins bearing a Weinreb amide group. (C) 2011 Elsevier Ltd. All rights reserved.

키워드

Cross-metathesis; Allyl halide; Weinreb amide; Grubbs-Hoveyda-Blechert 2nd generation catalyst; ASYMMETRIC TOTAL-SYNTHESIS; STRUCTURE REVISION; STEREOSELECTIVE-SYNTHESIS; ABSOLUTE STEREOCHEMISTRY; EFFICIENT; RUCL2(=CHR)(PR(3))(2); SUBGLUTINOLS; ASSIGNMENT; CATALYSTS; ALKENES

제목: Cross-metathesis of allyl halides with olefins bearing an α-alkoxy amide group

저자: Yun, Jeong In; Kim, Deukjoon; Lee, Jongkook

DOI: 10.1016/j.tetlet.2011.02.043

발행일: 2011-04-20

유형: Article

저널명: Tetrahedron Letters

권: 52

호: 16

페이지: 1928 ~ 1930