Terpene-Derived Bifunctional Thioureas in Asymmetric Organocatalysis

Autor(es)

Narayanaperumal, Senthil ^[1] ; Rivera, Daniel G. ^{[1, 2]} ; Silva, Rodrigo C. ^[1] ; Paixao, Marcio W. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Fed Sao Carlos, Dept Quim, BR-97105900 Sao Carlos, SP - Brazil

^[2] Univ Havana, Fac Chem, Ctr Nat Prod Res, Havana 10400 - Cuba

• Tipo de documento: Artigo de Revisão
• Fonte: CHEMCATCHEM; v. 5, n. 10, p. 2756-2773, OCT 2013.
• Citações Web of Science: 56

Resumo

Chiral hydrogen-bond donors have played a crucial role in the progress of asymmetric catalysis as an essential tool in modern organic synthesis. Among these donors, thioureas have been found to be one of the most powerful systems in organocatalytic approaches. Within the last three years, a new generation of bifunctional thiourea catalysts has emerged as an effective way to promote highly demanding chemical transformations, frequently with success rates that are intriguingly higher than with other traditional thioureas. This new class of organocatalysts incorporates a bulky, rigid, and chiral terpene skeleton as one of the thiourea substituents, thus providing an additional and effective rigidifying (entropic) effect on the electrophile activation profile of thioureas. Structural integrations, either with additional Lewis basic nucleophile-activating motifs or with amino groups for enamine catalysis, have enabled their implementation in a wide repertoire of stereocontrolled catalytic processes. This Review charts the development of these new catalysts, as well as their applications in a wide variety of reactions and reaction sequences, with the hope of encouraging further progress in the field of thiourea-catalyst discovery and of bringing attention to the countless possibilities that are opened up by the tremendous success of terpene-derived thiourea catalysts. (AU)

• Processo FAPESP: 11/01055-8 - Organocatálise: uma excelente ferramenta para síntese de moléculas bioativas
• Beneficiário: Senthil Narayanaperumal
• Modalidade de apoio: Bolsas no Brasil - Pós-Doutorado
• Processo FAPESP: 09/07281-0 - Organocatálise assimétrica: preparação de novos organocatalisadores e desenvolvimento de novas metodologias
• Beneficiário: Márcio Weber Paixão
• Modalidade de apoio: Auxílio à Pesquisa - Jovens Pesquisadores