Ruthenium-catalyzed cis-dihydroxylation of alkenes: Scope and limitations

Tony K.M. Shing, Eric K.W. Tam, Vincent W.F. Tai, Ivan H.F. Chung, Qin Jiang

研究成果: Article査読

165 被引用数 (Scopus)

抄録

Oxidative ruthenium catalysis (0.07 molequiv RuCl3· (H2O)3, 1.5 molequiv NaIO4, EtOAc/CH 3CN/H2O 3:3:1), beyond the usual C-C bond cleavage to give dicarbonyls, has been shown to syn-dihydroxylate a wide range of alkenes (except for strained bicyclic alkenes, sterically hindered trisubstituted alkenes, and most tetrasubstituted alkenes) to give vicinal diols rapidly (within minutes) and efficiently. The minor products are the usual oxidative fission products, namely, ketones and aldehydes or carboxylic acids, and sometimes ketols. Longer reaction times lower the yields of most diols, probably owing to oxidative glycol cleavage. Reactions with substrates containing one or more electron-with-drawing groups in conjugation with or adjacent to the alkene moiety are generally slower but give better yields. The diastereoselectivity of the present "flash" dihydroxylation, anti to the existing α-stereogenic center, with cycloalkenes is excellent whereas that with acyclic alkenes is moderate to poor. Sodium metaperio-date is still the best co-oxidant for the catalytic reaction. Aqueous acetonitrile (approximately 86%) as an alternative solvent system was found to give better yields of 1,2-diols than the original solvent system in some cases.

本文言語English
ページ(範囲)50-57
ページ数8
ジャーナルChemistry - A European Journal
2
1
DOI
出版ステータスPublished - 1996 12月 1

ASJC Scopus subject areas

  • 触媒
  • 化学 (全般)
  • 有機化学

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