Asymmetric Intermolecular Rauhut−Currier Reaction for the Construction of 3, 3‐Disubstituted Oxindoles with Quaternary Stereogenic Centers. Issue 22 (27th September 2017)

• Record Type: Journal Article
• Authors: Wang, Hongyu; Wang, Kaiye; Man, Yunquan; Gao, Xiaonan; Yang, Limin; Ren, Yanfei; Li, Na; Tang, Bo; Zhao, Gang
• Is Part Of: Advanced synthesis & catalysis. Volume 359:Issue 22(2017)
• Page Start: 3934
• Page End: 3939
• Publication Date: 2017-09-27
• Subjects: Rauhut−Currier reaction -- quaternary stereocenters -- remote stereogenic center -- asymmetric catalysis -- organocatalysis; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201700649
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A remote cross Rauhut−Currier reaction utilizing vinyl ketones and para ‐quinone methides derived from isatins was realized, which was successfully catalyzed using bifunctional phosphines, furnishing chiral 3, 3‐disubstituted oxindoles in excellent enantioselectivities and high yields. The mechanistic studies demonstrated the key role of the alkyl hydrogen of the vinyl ketones, which conceivably interacted with the para ‐quinone methide carbonyl group via the hydrogen bond, offering a new insight for the design of novel asymmetric reactions. Abstract :