Development of C 2‑Symmetric Chiral Bifunctional Triamines: Synthesis and Application in Asymmetric Organocatalysis

The synthesis and application of a newly designed C 2-symmetric chiral bifunctional triamine family (C 2-CBT) is reported. These enantiopure chiral triamine scaffolds can be accessed in multigram amounts from simple amino acids while avoiding chromatographic purification. As a proof of principle, C...

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Bibliographic Details
Published inOrganic letters Vol. 20; no. 16; pp. 4806 - 4810
Main Authors Cañellas, Santiago, Alonso, Pedro, Pericàs, Miquel À
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.08.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ENANTIOSELECTIVE ALDOL REACTION
COOPERATIVE CATALYSIS
TI-MEDIATED ADDITION
ISATINS
DIETHYLZINC
CONDENSATION
CYANOSILYLATION
PROTEASOME INHIBITORS
FORMALDEHYDE
DERIVATIVES
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Summary:The synthesis and application of a newly designed C 2-symmetric chiral bifunctional triamine family (C 2-CBT) is reported. These enantiopure chiral triamine scaffolds can be accessed in multigram amounts from simple amino acids while avoiding chromatographic purification. As a proof of principle, C 2-CBT has been studied in the aldol reaction of cyclic ketones with isatins, with the target tertiary alcohols being formed in a highly efficient manner. Catalyst recovery by simple extraction techniques and subsequent reuse has been performed.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b01957