Enantioselective Formal C(sp2)−H Vinylation. Issue 42 (7th September 2016)

• Record Type: Journal Article
• Authors: Manna, Madhu Sudan; Sarkar, Rahul; Mukherjee, Santanu
• Is Part Of: Chemistry. Volume 22:Issue 42(2016)
• Page Start: 14912
• Page End: 14919
• Publication Date: 2016-09-07
• Subjects: C−H functionalization -- decarboxylation -- desymmetrization -- lactones -- vinylation; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201602253
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: An enantioselective formal C(sp 2 )−H vinylation of prochiral 2, 2‐disubstituted cyclopentene‐1, 3‐dione is presented. This vinylative desymmetrization is realized by using a two‐step procedure that consists of a catalytic enantioselective vinylogous Michael addition of deconjugated butenolides to cyclopentene‐1, 3‐dione and a base‐mediated decarboxylation. The overall process utilizes deconjugated butenolides as the source of the highly substituted vinyl unit. Five‐membered carbocycles containing a remote all‐carbon quaternary stereogenic center are obtained in good yields and with good to high enantioselectivities. Abstract : Vinyl destination : An enantioselective formal C(sp 2 )−H vinylation of prochiral 2, 2‐disubstituted cyclopentene‐1, 3‐dione is realized using a two‐step procedure, which utilizes deconjugated butenolides as the source of highly substituted vinyl unit and delivers five‐membered carbocycles containing a remote all‐carbon quaternary stereogenic center in good yields and with good to high enantioselectivities.