Catalytic Enantioselective and Regioselective [3+3] Cycloadditions Using 2-Indolylmethanols as 3 C Building Blocks

• Published in: Chemistry : a European journal 2016-12, Vol.22 (49), p.17526-17532
• Main Authors: Sun, Xiao-Xue, Zhang, Hong-Hao, Li, Guo-Hao, He, Ying-Ying, Shi, Feng
• Format: Article
• Language: English
• Subjects: asymmetric catalysis; azomethine ylide; Catalysis; cycloaddition; Cycloaddition Reaction; enantioselectivity; Indoles - chemistry; Molecular Structure; organocatalysis; Stereoisomerism
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201603049

The first catalytic asymmetric cycloaddition using 2‐indolylmethanols as 3C building blocks has been established by a chiral phosphoric acid‐catalyzed enantioselective and regioselective [3+3] cycloaddition of 2‐indolylmethanols with azomethine ylides, which constructed biologically important tetrahydro‐γ‐carboline frameworks in high yields and excellent enantioselectivities (up to 83 % yield, 99:1 e.r.). This reaction not only represents the first application of 2‐indolylmethanols as 3C building blocks in catalytic asymmetric cycloadditions, but also has established an abnormal regioselectivity in indolylmethanol‐involved transformations. Abnormally selective: The first catalytic asymmetric cycloaddition using 2‐indolylmethanols as 3 C building blocks has been established by chiral phosphoric acid catalyzed enantioselective and regioselective [3+3] cycloaddition of 2‐indolylmethanols with azomethine ylides, which constructed biologically important tetrahydro‐γ‐carboline frameworks in high yields and excellent enantioselectivities (up to 83 % yield, 99:1 e.r.).