Organocatalytic Asymmetric Vinylogous Michael Addition of Dicyanoolefins to Imine Intermediates Generated in situ from Arenesulfonylalkylindoles

• Published in: Advanced synthesis & catalysis Vol. 354; no. 16; pp. 2965 - 2970
• Main Authors: Zhu, Xing-Li, He, Wu-Jun, Yu, Liang-Liang, Cai, Chang-Wu, Zuo, Zong-Le, Qin, Da-Bin, Liu, Quan-Zhong, Jing, Lin-Hai
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 12.11.2012; WILEY‐VCH Verlag; Wiley; Wiley-VCH
• Subjects: Adducts; arenesulfonylalkylindoles; asymmetric catalysis; Asymmetry; Catalysis; Catalysts: preparations and properties; Chemistry; Chemistry, Applied; Chemistry, Organic; Derivatives; dicyanoolefins; Exact sciences and technology; General and physical chemistry; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Imines; Indoles; Ketones; Michael reaction; organic catalysis; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Synthesis; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; vinylogous Michael addition; dicyanoolefins; ENANTIOSELECTIVE SYNTHESIS; NATURAL-PRODUCTS; BETA-SUBSTITUTED TRYPTOPHANS; 3-(1-ARYLSULFONYLALKYL) INDOLES; ALDOL REACTIONS; arenesulfonylalkylindoles; asymmetric catalysis; CARBON BOND FORMATION; ALPHA-AMIDO SULFONES; MANNICH REACTION; organic catalysis; vinylogous Michael addition; ARYLSULFONYL INDOLES; FRIEDEL-CRAFTS ALKYLATION; Michael addition; Catalytic reaction; Enantioselectivity; Nitrogen heterocycle; Organocatalyst; Imine; Asymmetric catalysis; Ketone; Alkylation; Diastereoselectivity; Asymmetric synthesis; Vinylic compound; Enantiomeric excess; Indole derivatives
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.201200286

An organocatalytic asymmetric vinylogous Michael addition of dicyanoolefins to vinylogous imine intermediates generated in situ from arenesulfonylalkylindoles has been developed. This protocol provides an easy and convenient approach to C‐3 alkyl‐substituted indole derivatives with high yields (up to 93%), diastereomeric ratios (up to 99:1 dr) and enantioselectivities (up to 99% ee). The resulting adducts can be also readily converted to pyrazolo derivatives or α‐alkylation products of ketones without any decrease of the diastereoselectivities and enantioselectivities.