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Three-component asymmetric catalytic Ugi reaction--concinnity from diversity by substrate-mediated catalyst assembly.

ABSTRACT: The first chiral catalyst for the three-component Ugi reaction was identified as a result of a screen of a large set of different BOROX catalysts. The BOROX catalysts were assembled in?situ from a chiral biaryl ligand, an amine, water, BH3·SMe2, and an alcohol or phenol. The catalyst screen included 13 different ligands, 12 amines, and 47 alcohols or phenols. The optimal catalyst system (LAP 8-5-47) provided ?-amino amides from an aldehyde, a secondary amine, and an isonitrile with excellent asymmetric induction. The catalytically active species is proposed to be an ion pair that consists of the chiral boroxinate anion and an iminium cation.

SUBMITTER: Zhao W

PROVIDER: S-EPMC4010135 | biostudies-literature | 2014 Mar

REPOSITORIES: biostudies-literature

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Three-component asymmetric catalytic Ugi reaction--concinnity from diversity by substrate-mediated catalyst assembly.

Zhao Wenjun W Huang Li L Guan Yong Y Wulff William D WD

Angewandte Chemie (International ed. in English) 20140219 13

The first chiral catalyst for the three-component Ugi reaction was identified as a result of a screen of a large set of different BOROX catalysts. The BOROX catalysts were assembled in situ from a chiral biaryl ligand, an amine, water, BH3·SMe2, and an alcohol or phenol. The catalyst screen included 13 different ligands, 12 amines, and 47 alcohols or phenols. The optimal catalyst system (LAP 8-5-47) provided α-amino amides from an aldehyde, a secondary amine, and an isonitrile with excellent asy ...[more]

PMID: 24554529

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