Chiral Bicyclic Imidazole‐Catalyzed Direct Enantioselective C‐Acylation for the Synthesis of 2‐Oxindoles Bearing a Quaternary Stereocenter. Issue 7 (4th July 2019)

• Record Type: Journal Article
• Authors: Zhang, Lu; Wang, Mo; Zhou, Muxing; Zhang, Zhenfeng; Muraoka, Masahiro; Zhang, Wanbin
• Is Part Of: Asian journal of organic chemistry. Volume 8:Issue 7(2019)
• Page Start: 1024
• Page End: 1028
• Publication Date: 2019-07-04
• Subjects: acylation -- oxindoles -- quaternary stereocenters -- enantioselectivity -- organocatalysis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201900294
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: A direct enantioselective C‐acylation of N ‐ protected 3‐substituted‐2‐oxindoles has been developed for the synthesis of chiral N‐protected 2‐oxindoles bearing a 3‐acyl‐substituted quaternary stereocenter. Catalyzed by a chiral bicyclic imidazole organocatalyst, the target compounds were synthesized with high reactivity, good enantioselectivity of up to 88% ee, and low catalyst loading of down to 1 mol%. Abstract : Being direct can be good : Catalyzed by a chiral bicyclic imidazole, a direct enantioselective C‐acylation of 3‐substituted‐2‐oxindoles has been developed for the synthesis of a series of 3, 3‐disubstituted oxindoles possessing a quaternary stereocenter. The reaction has the advantages of good enantioselectivity, high reactivity, and low catalyst loading.