Double diastereocontrol in bifunctional thiourea organocatalysis: Iterative Michael-Michael-Henry sequence regulated by the configuration of chiral catalysts

Szilárd Varga, Gergely Jakab, László Drahos, Tamás Holczbauer, Mátyás Czugler, Tibor Soós

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Abstract

The importance and reactivity consequences of the double diastereocontrol in noncovalent bifunctional organocatalysis were studied. The results suggest that the bifunctional thioureas can have synthetic limitations in multicomponent domino or autotandem catalysis. Nevertheless, we provided a means to exploit this behavior and used the configuration of the chiral catalyst as a control element in organo-sequential reactions.

Original languageEnglish
Pages (from-to)5416-5419
Number of pages4
JournalOrganic Letters
Volume13
Issue number20
DOIs
Publication statusPublished - Oct 21 2011

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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