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
Hauptverfasser: Shi, Yan, Lin, Aijun, Mao, Haibin, Mao, Zhijie, Li, Weipeng, Hu, Hongwen, Zhu, Chengjian, Cheng, Yixiang
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.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201202937