Chiral N,N′-Dioxide-Organocatalyzed Regio-, Diastereo- and Enantioselective Michael Addition-Alkylation Reaction

• Published in: Chemistry : a European journal Vol. 22; no. 44; pp. 15650 - 15653
• Main Authors: Feng, Juhua, Yuan, Xiao, Luo, Weiwei, Lin, Lili, Liu, Xiaohua, Feng, Xiaoming
• Format: Journal Article
• Language: English
• Published: WEINHEIM Blackwell Publishing Ltd 24.10.2016; Wiley; Wiley Subscription Services, Inc
• Subjects: 2,3-dihydrofuran; 3-dihydrofuran; asymmetric catalysis; Chemistry; Chemistry, Multidisciplinary; chiral N; chiral N,N′-dioxide; Michael alkylation; N′-dioxide; organocatalysis; Physical Sciences; Science & Technology; DOMINO REACTION; N-dioxide; ASYMMETRIC TRANSFER HYDROGENATION; AMINO-ALCOHOLS; ONE-POT; DIAZO-COMPOUNDS; asymmetric catalysis; Michael alkylation; 3-dihydrofuran; CASCADE REACTION; organocatalysis; HIGHLY FUNCTIONALIZED DIHYDROFURANS; 2; KINETIC RESOLUTION; 4+1 CYCLOADDITIONS; chiral N; STEREOSELECTIVE-SYNTHESIS; chiral N,N′-dioxide; 2,3-dihydrofuran
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201603629

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. 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.