Control of Remote Stereochemistry in the Synthesis of Spirocyclic Oxindoles: Vinylogous Organocascade Catalysis

Remote control: The title reaction facilitates the synthesis of complex chiral molecules while selectively forging multiple stereocenters at distant positions, namely five and six bond lengths away from the catalyst chiral fragment (see scheme; Boc=tert‐butoxycarbonyl). The potential of the strategy...

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Veröffentlicht in:Angewandte Chemie International Edition 2013-05, Vol.52 (20), p.5360-5363
Hauptverfasser: Tian, Xu, Melchiorre, Paolo
Format: Artikel
Sprache:eng
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Zusammenfassung:Remote control: The title reaction facilitates the synthesis of complex chiral molecules while selectively forging multiple stereocenters at distant positions, namely five and six bond lengths away from the catalyst chiral fragment (see scheme; Boc=tert‐butoxycarbonyl). The potential of the strategy is demonstrated through the one‐step preparation of spirocyclopentane oxindoles having four contiguous stereocenters.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201301017