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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Metal-Free Synthesis of Homopropargylic Alcohols from Aldehydes

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Author(s):
Teodoro, Bruno V. M. [1] ; Silva, Jr., Luiz F. [1]
Total Authors: 2
Affiliation:
[1] Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, BR-05508000 Sao Paulo, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: Journal of Organic Chemistry; v. 82, n. 22, p. 11787-11791, NOV 17 2017.
Web of Science Citations: 4
Abstract

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)

FAPESP's process: 15/00527-4 - Hypervalent iodine: methodology and total synthesis
Grantee:Luiz Fernando da Silva Júnior
Support Opportunities: Regular Research Grants