ChemInform Abstract: Dual Organocatalytic Activation of Isatins and Formaldehyde tert-Butyl Hydrazone: Asymmetric Synthesis of Functionalized 3-Hydroxy-2-oxindoles

Dual activation of isatins and formaldehyde tert‐butyl hydrazone by 2,2′‐diamino‐1,1′‐binaphthalene (BINAM)‐derived bis(ureas) is the key to achieve high reactivity and excellent enantioselectivities in the synthesis of azo‐functionalized 3‐hydroxy‐2‐oxindoles.

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Bibliographic Details
Published inChemInform Vol. 44; no. 46; p. no
Main Authors Monge, David, Crespo-Pena, Ana M., Martin-Zamora, Eloisa, Alvarez, Eleuterio, Fernandez, Rosario, Lassaletta, Jose M.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 12.11.2013
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
Subjects
C-C bond formation
diastereoselective syntheses
diastereoselective syntheses, enantioselective syntheses (incl. cis/trans‐isomerism)
enantioselective syntheses (incl. cis/trans-isomerism)
indole derivatives
indole derivatives, isoindole derivatives
isoindole derivatives
organocatalysis
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Summary:Dual activation of isatins and formaldehyde tert‐butyl hydrazone by 2,2′‐diamino‐1,1′‐binaphthalene (BINAM)‐derived bis(ureas) is the key to achieve high reactivity and excellent enantioselectivities in the synthesis of azo‐functionalized 3‐hydroxy‐2‐oxindoles.
Bibliography:istex:8FD0A026C52B7B752AD5DB1620E85EDB027CCEEF
ArticleID:CHIN201346110
ark:/67375/WNG-TKRC7GJJ-M
ISSN:0931-7597
1522-2667
DOI:10.1002/chin.201346110