An Eco‐Friendly Asymmetric Organocatalytic Conjugate Addition of Malonates to α, β‐Unsaturated Aldehydes: Application on the Synthesis of Chiral Indoles. Issue 26 (26th July 2013)

• Record Type: Journal Article
• Authors: Feu, Karla Santos; Deobald, Anna Maria; Narayanaperumal, Senthil; Corrêa, Arlene G.; Weber Paixão, Márcio
• Is Part Of: European journal of organic chemistry. Issue 26(2013)
• Page Start: 5917
• Page End: 5922
• Publication Date: 2013-07-26
• Subjects: Synthetic methods -- Organoca­talysis -- Michael addition -- Green chemistry -- Nitrogen heterocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300431
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: The asymmetric Michael addition of malonates to α, β‐unsaturated aldehydes using a modified Jørgensen–Hayashi organocatalyst in EtOH:brine solvent media is reported. The procedure proceeds smoothly to afford the corresponding Michael adducts in good yields with excellent enantioselectivities. The resulting Michael adducts represent excellent building blocks for the synthesis of chiral indoles. Abstract : The asymmetric Michael reaction using a modified Jørgensen–Hayashi organocatalyst in EtOH:brine solvent media is reported. This procedure afforded the corresponding Michael adducts in good yields and with excellent enantioselectivities. The resulting adducts were further used as chiral building blocks for the synthesis of indoles.