Organocatalytic Asymmetric Mannich Reaction of 3-Hydroxyoxindoles/3-Aminooxindoles with in Situ Generated N-Boc-Protected Aldimines for the Synthesis of Vicinal Oxindole–Diamines/Amino Alcohols

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• 作者：Jing Shan ; Baodong Cui ; Yu Wang ; Chengli Yang ; Xiaojian Zhou ; Wenyong Han ; Yongzheng Chen
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：July 1, 2016
• 年：2016
• 卷：81
• 期：13
• 页码：5270-5277
• 全文大小：386K
• 年卷期：0
• ISSN：1520-6904

文摘

A highly efficient asymmetric Mannich reaction of 3-monosubstituted 3-aminooxindoles/3-hydroxyoxindoles with in situ generated N-Boc-protected aldimines catalyzed by the chiral bifunctional thiourea–tertiary amine catalyst has been developed. Under mild reaction conditions, a series of structurally diverse vicinal oxindole–diamines/amino alcohols were smoothly obtained in moderate to high yields (up to 99%) with good to excellent diastereoselectivities and enantioselectivities (up to 95:5 dr and 96% ee). The synthetic application of this protocol was also demonstrated by the versatile transformation of chiral vicinal oxindole–diamine/amino alcohol into spirocyclic oxindoles.