Asymmetric Synthesis of Chiral α‐CF2H Spiro[Indoline‐3, 3′‐Thiophene] via Phase‐Transfer Catalyzed Sulfa‐Michael/Michael Domino Reaction. Issue 4 (29th December 2021)

• Record Type: Journal Article
• Authors: Deng, Yabo; Sun, Shuo; Wang, Yuqiang; Jia, Pengfeng; Li, Wenguang; Wang, Kairong; Yan, Wenjin
• Is Part Of: Advanced synthesis & catalysis. Volume 364:Issue 4(2022)
• Page Start: 811
• Page End: 830
• Publication Date: 2021-12-29
• Subjects: Phase-Transfer Catalyst -- CF2H -- spiro[indoline-3, 3′-thiophene]s -- vicinal quaternary stereocenters -- Sulfa-Michael/Michael domino reaction; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202101320
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: An asymmetric Sulfa‐Michael/Michael domino reaction of ( E )‐4‐mercapto‐2‐butenoates with difluoromethyl‐eneoxindoles catalyzed by a quinidine‐derived ammonium salts as phase transfer catalyst has been disclosed. Under mild conditions, a broad range of CF2 H‐containing spiro[indoline‐3, 3′‐thiophene]s, bearing three adjacent chiral centers including two vicinal spiro quaternary stereocenters, catalysed by only 5 mol% PTC catalyst were obtained in yields of 75–98%, excellent diastereoselectivities (>20:1, in almost all cases) and enantioselectivities of 19–98% in short reaction times (almost less than 20 minutes). Abstract :