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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.)

Sequential Michael Addition/Electrophilic Alkynylation: Synthesis of alpha-Alkynyl-beta-Substituted Ketones and Chromanones

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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 - Brazil
Total Affiliations: 1
Document type: Journal article
Source: Journal of Organic Chemistry; v. 83, n. 21, p. 13604-13611, NOV 2 2018.
Web of Science Citations: 1
Abstract

We describe the synthesis of alpha-alkynyl-beta-substituted cyclic ketones and analogue chromanones via one-pot Michael addition/hypervalent iodine-based alpha-alkynylation. Cu(I)-catalyzed Michael addition using either alkyl-aluminum or Grignard reagents, followed by diastereoselective electrophilic alkynylation of the resulting enolate by 1-ethynyl-1 lambda(3),2-benziodoxol-3(1H)-one (EBX) resulted in the alpha-alkynyl-beta-substituted cyclic ketones or chromanones within 34-89% yield (16 examples). The reaction was successfully upscaled to the 5 mmol scale, and further functionalization of a model alkynylated ketone was demonstrated. (AU)

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