Application of 7‐Indolylmethanols in Catalytic Asymmetric Arylations with Tryptamines: Enantioselective Synthesis of 7‐indolylmethanes

• Published in: Advanced synthesis & catalysis Vol. 360; no. 9; pp. 1850 - 1860
• Main Authors: Wang, Hai‐Qing, Xu, Meng‐Meng, Wan, Ying, Mao, Yu‐Jia, Mei, Guang‐Jian, Shi, Feng
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 02.05.2018; Wiley Subscription Services, Inc
• Subjects: Arylation; asymmetric organocatalysis; Asymmetry; Catalysis; Chemical synthesis; Chemistry; Chemistry, Applied; Chemistry, Organic; chiral phosphoric acid; enantioselectivity; indolylmethanol; Phosphoric acid; Physical Sciences; Science & Technology; tryptamine; Tryptamines; asymmetric organocatalysis; enantioselectivity; Arylation; C(SP)-H BONDS; CASCADE REACTIONS; chiral phosphoric acid; indolylmethanol; INDOL-2-YL CARBINOLS; tryptamine; TERTIARY ALCOHOLS; IN-VITRO EVALUATION; PHOSPHORIC-ACID; ALPHA-ALKYLATION; FRIEDEL-CRAFTS ALKYLATION; CYCLOADDITION REACTION; BRONSTED-ACID
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.201800150

The application of 7‐indolylmethanols in catalytic asymmetric reactions has been established via an enantioselective arylation reaction with tryptamines in the presence of chiral phosphoric acid, which afforded a series of structurally diversified chiral 7‐indolylmethanes in moderate to good yields and generally excellent enantioselectivities (23 examples, up to 92% ee). This reaction not only provides a useful strategy for the enantioselective synthesis of chiral 7‐indolylmethanes, but also represents a good example of 7‐indolylmethanol‐involved catalytic asymmetric reaction, which will greatly enrich the chemistry of indolylmethanols.