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

  • Yun, Jeong In
  • Kim, Hyoung Rae
  • Kim, Sang Kyum
  • Kim, Deukjoon
  • Lee, Jongkook
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초록

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. (C) 2011 Elsevier Ltd. All rights reserved.

키워드

Cross-metathesisAllyl halideWeinreb amideGrubbs-Hoveyda-Blechert second generation catalystASYMMETRIC TOTAL-SYNTHESISSTRUCTURE REVISIONSTEREOSELECTIVE-SYNTHESISABSOLUTE STEREOCHEMISTRYEFFICIENTRUCL2(=CHR)(PR(3))(2)SUBGLUTINOLSASSIGNMENTCATALYSTSCONCISE
제목
Cross-metathesis of allyl halides with olefins bearing amide and ester groups
저자
Yun, Jeong InKim, Hyoung RaeKim, Sang KyumKim, DeukjoonLee, Jongkook
DOI
10.1016/j.tet.2011.11.064
발행일
2012-01-28
유형
Article
저널명
Tetrahedron
68
4
페이지
1177 ~ 1184