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Angewandte Chemie International Edition

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

Authors


  • Research support from the ICIQ Foundation, MICINN (grant CTQ2010-15513), and the European Research Council (ERC Starting Grant to PM, agreement no. 278541—ORGA-NAUT) is gratefully acknowledged. The authors thank Grace Fox for proofreading the manuscript, Eduardo Escudero-Adán for X-ray crystallographic analysis, and Dr. Yankai Liu for fruitful discussions.

Abstract

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.

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