Catalytic Asymmetric Conjugate Addition of Indolizines to alpha,beta-Unsaturated Ketones

Author(s)

Menezes Correia, Jose Tiago ; List, Benjamin ; Coelho, Fernando

• Document type: Journal article
• Source: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION; v. 56, n. 27, p. 7967-7970, JUN 26 2017.
• Web of Science Citations: 34

Abstract

A catalytic enantioselective conjugate addition of indolizines to enones is described. The chiral phosphoric acid (S)-TRIP activates alpha,beta-unsaturated ketones, thereby promoting an enantioface-differentiating attack by indolizines. Using this reaction, several alkylated indolizines were synthesized in good yields and with enantiomeric ratios of up to 98:2. (AU)

• FAPESP's process: 13/10449-5 - Morita-Baylis-Hillman adducts as efficient building blocks for the synthesis of molecules of biological interest
• Grantee: Fernando Antonio Santos Coelho
• Support Opportunities: Regular Research Grants
• FAPESP's process: 14/02062-6 - Exploring the ACDC concept on hydrogenation and Friedel-Crafts reactions using indolizines obtained from Morita-Baylis-Hillman adducts
• Grantee: José Tiago Menezes Correia
• Support Opportunities: Scholarships abroad - Research Internship - Doctorate
• FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
• Grantee: Glaucius Oliva
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC