Osmium-catalyzed olefin dihydroxylation and aminohydroxylation in the second catalytic cycle

Peng Wu, Robert Hilgraf, Valery V. Fokin

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20 Citations (Scopus)

Abstract

Two catalytic cycles operate in the osmium-catalyzed olefin dihydroxylation and aminohydroxylation. Slow hydrolysis of the Os(VI) monoglycolate (or monoazaglycolate in aminohydroxylation) intermediate often results in the addition of another molecule of olefin thereby shunting the catalysis into the second catalytic cycle. As a result, both enantio- and chemoselectivity are reduced. A series of new chelating ligands were devised, which force the catalysis into the second cycle while maintaining enantiocontrol in the olefin addition step. Excellent catalytic turnover and moderate to good enantioselectivity were achieved.

Original languageEnglish
Pages (from-to)1079-1085
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume348
Issue number9
DOIs
Publication statusPublished - Jun 2006
Externally publishedYes

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Keywords

  • Alkenes
  • Aminohydroxylations
  • Asymmetric catalysis
  • Dihydroxylations
  • Osmium

ASJC Scopus subject areas

  • Chemistry (miscellaneous)
  • Organic Chemistry
  • Catalysis

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