Highly Enantioselective Organocatalytic Sulfenylation of 3-Aryloxindoles

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• 作者：Zhiqiang Han ; Wenchao Chen ; Sheng Dong ; Caiyun Yang ; Hongjun Liu ; Yuanhuang Pan ; Lin Yan ; Zhiyong Jiang
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：September 7, 2012
• 年：2012
• 卷：14
• 期：17
• 页码：4670-4673
• 全文大小：231K
• 年卷期：v.14,no.17(September 7, 2012)
• ISSN：1523-7052

文摘

An organocatalytic asymmetric sulfenylation of 3-aryloxindoles with N-(sulfanyl)succinimides has been developed by using commercially available (DHQD)₂PHAL as catalyst. Various chiral 3-benzylthio-, alkylthio-, and arylthio-substituted oxindoles, containing 3,3-disubstituted quarternary carbon stereocenters, could be obtained in high enantioselectivities (85鈥?7% ee). Furthermore, the opposite enantiomers of the sulfenylated products were readily accessible with equal excellent enantioselectivities (86鈥?5% ee) by replacing the catalyst with (DHQ)₂PHAL.