Enantioselective Construction of Spirooxindole Derivatives through [3+2] Annulation Catalyzed by a Bisthiourea as a Multiple-Hydrogen-Bond Donor
Anything between ureas? Spiro[isoxazolidine‐3,3′‐oxindole]s have been constructed by employing methyleneindolinones and nitrones as the starting materials through [3+2] annulation catalyzed by a bisthiourea. Products with three contiguous stereocenters, including one spiroquaternary stereocenter, ar...
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Veröffentlicht in: | Chemistry : a European journal 2013-02, Vol.19 (6), p.1914-1918 |
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Hauptverfasser: | , , , , , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | Anything between ureas? Spiro[isoxazolidine‐3,3′‐oxindole]s have been constructed by employing methyleneindolinones and nitrones as the starting materials through [3+2] annulation catalyzed by a bisthiourea. Products with three contiguous stereocenters, including one spiroquaternary stereocenter, are obtained in good yields with excellent enantio‐ and diastereoselectivity. The bisthiourea catalyst acts as a multiple‐hydrogen‐bond donor to simultaneously activate both substrates. |
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ISSN: | 0947-6539 1521-3765 |
DOI: | 10.1002/chem.201202937 |