Catalytic Asymmetric Construction of Spirocyclopentaneoxindoles by a Combined Ru-Catalyzed Cross-Metathesis/Double Michael Addition Sequence

Biologically important and synthetically challenging spirocyclopentaneoxindoles with four contiguous stereocenters including one spiroquaternary stereocenter have been constructed in good yields (72–87%) with excellent diastereoselectivity (16:1→30:1 dr) and enantioselectivity (93→99% ee) by a combi...

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Veröffentlicht in:	Organic letters 2011-12, Vol.13 (23), p.6200-6203
Hauptverfasser:	Li, Ying-Mei, Li, Xiang, Peng, Fang-Zhi, Li, Ze-Qian, Wu, Shou-Tao, Sun, Zhong-Wen, Zhang, Hong-Bin, Shao, Zhi-Hui
Format:	Artikel
Sprache:	eng
Schlagworte:	Catalysis Combinatorial Chemistry Techniques Cyclopentanes - chemical synthesis Cyclopentanes - chemistry Indoles - chemical synthesis Indoles - chemistry Molecular Structure Ruthenium - chemistry Spiro Compounds - chemical synthesis Spiro Compounds - chemistry Stereoisomerism
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Beschreibung
Zusammenfassung:	Biologically important and synthetically challenging spirocyclopentaneoxindoles with four contiguous stereocenters including one spiroquaternary stereocenter have been constructed in good yields (72–87%) with excellent diastereoselectivity (16:1→30:1 dr) and enantioselectivity (93→99% ee) by a combined Ru-catalyzed cross-metathesis/organocatalyzed asymmetric double-Michael addition sequence.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol202624f