Metal-Free Synthesis of Homopropargylic Alcohols from Aldehydes

Autor(es)

Teodoro, Bruno V. M. ^[1] ; Silva, Jr., Luiz F. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, BR-05508000 Sao Paulo, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Journal of Organic Chemistry; v. 82, n. 22, p. 11787-11791, NOV 17 2017.
• Citações Web of Science: 4

Resumo

The synthesis of homopropargylic alcohols under metal-free and mild condition is described. This transformation is based on a one-pot procedure involving sequential alpha-alkynylation of acyclic aldehydes using hyper-valent iodine reagents and borohydride reduction. The chemistry exhibits broad substrate scope and good scalability, providing a convenient route for the alpha-alkynylation of aldehydes along with the formation of a quaternary carbon center. The applicability of the method is demonstrated by the gram-scale synthesis of the key synthetic precursor of botulinum toxin inhibitors. (AU)

• Processo FAPESP: 15/00527-4 - Iodo hipervalente: metodologia e síntese total
• Beneficiário: Luiz Fernando da Silva Júnior
• Modalidade de apoio: Auxílio à Pesquisa - Regular