Chiral N, N′‐Dioxide‐Organocatalyzed Regio‐, Diastereo‐ and Enantioselective Michael Addition–Alkylation Reaction. Issue 44 (30th September 2016)

• Record Type: Journal Article
• Authors: Feng, Juhua; Yuan, Xiao; Luo, Weiwei; Lin, Lili; Liu, Xiaohua; Feng, Xiaoming
• Is Part Of: Chemistry. Volume 22:Issue 44(2016)
• Page Start: 15650
• Page End: 15653
• Publication Date: 2016-09-30
• Subjects: 2, 3-dihydrofuran -- asymmetric catalysis -- chiral N, N′-dioxide -- Michael alkylation -- organocatalysis; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201603629
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A highly regio‐, diastereo‐ and enantioselective Michael addition–alkylation reaction between α‐substituted cyano ketones and ( Z )‐bromonitrostyrenes has been realized by using a chiral N, N ′‐dioxide as organocatalyst. A variety of substrates performed well in this reaction, and the corresponding multifunctionalized chiral 2, 3‐dihydrofurans were obtained in up to 95 % yield with 95:5 dr and 93 % ee . Abstract : Magic Mike : The catalytic asymmetric Michael addition/O‐alkylation reaction of ( Z )‐bromonitrostyrenes with α‐substituted cyano ketones is accomplished by using an efficient N, N ′‐dioxide organocatalyst. A range of 2, 3‐dihydrofuran derivatives is obtained with high to excellent enantiomeric excesses and excellent diastereomeric ratios.