Asymmetric Synthesis of Dihydrofurans via Organocatalytic Domino Michael-Alkylation Reaction

• Published in: Advanced synthesis & catalysis Vol. 357; no. 6; pp. 1305 - 1310
• Main Authors: Feng, Juhua, Lin, Lili, Yu, Kunru, Liu, Xiaohua, Feng, Xiaoming
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 13.04.2015; WILEY‐VCH Verlag; Wiley
• Subjects: asymmetric catalysis; Asymmetry; Catalysis; Chemistry; Chemistry, Applied; Chemistry, Organic; chiral N; chiral N,N′‐dioxide; Derivatives; desymmetrization; dihydrofuran; domino Michael-alkylation reaction; N′-dioxide; organocatalysis; Physical Sciences; Science & Technology; Synthesis; HIGHLY ENANTIOSELECTIVE SYNTHESIS; desymmetrization; ACID; chiral N,N '-dioxide; DIAZO-COMPOUNDS; asymmetric catalysis; CASCADE REACTION; organocatalysis; REARRANGEMENT; domino Michael-alkylation reaction; FUNCTIONALIZED DIHYDROFURANS; CONSTRUCTION; 4+1 CYCLOADDITIONS; STEREOSELECTIVE-SYNTHESIS; 2,3-DIHYDROFURANS; dihydrofuran
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.201401198

The chiral N,N′‐dioxide C‐PrPr2 has been developed as an efficient organocatalyst to catalyze the asymmetric domino Michael–alkylation reaction between cyclohexane‐1,3‐dione derivatives and bromonitrostyrenes. For dimedone, the corresponding bicyclic 2,3‐dihydrofurans with two stereocenters were obtained in up to 99 % yield with 95:5 d.r. and 96 % ee. For prochiral 5‐monosubstituted cyclohexane‐1,3‐diones, the desymmetrization reaction provided the bicyclic 2,3‐dihydrofurans with three stereocenters in up to 90 % yield with 82:18 d.r. and 94 % ee.