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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.)

Synthesis of enyne and aryl vinyl sulfoxides: functionalization via Pummerer rearrangement

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Author(s):
Souza, Frederico B. [1] ; Shamim, Anwar [2] ; Argomedo, Luiz M. Z. [1] ; Pimenta, Daniel C. [3] ; Stefani, Helio A. [1]
Total Authors: 5
Affiliation:
[1] Univ Sao Paulo, Fac Ciencias Farmaceut, Dept Farm, Sao Paulo, SP - Brazil
[2] Univ Sao Paulo, Inst Quim, Sao Paulo, SP - Brazil
[3] Inst Butantan, Sao Paulo, SP - Brazil
Total Affiliations: 3
Document type: Journal article
Source: MOLECULAR DIVERSITY; v. 19, n. 4, p. 773-785, NOV 2015.
Web of Science Citations: 3
Abstract

An efficient methodology for the synthesis of aryl-substituted vinyl sulfoxides through direct substitution of aryl-substituted alkynyl grignard reagents on menthyl-p-toluenesulfinate followed by Suzuki-Miyaura cross-coupling reaction has been developed. It has also been described that the reaction of alkyl-substituted and cycloalkyl-substituted alkynyl grignard reagents with menthyl-p-toluenesulfinate led to two products, i.e., alkynyl sulfoxide derivatives, as a result of substitution, and enyne sulfoxide derivatives, which resulted from substitution followed by Michael type addition. It was possible to selectively synthesize the enyne sulfoxide derivatives by changing the concentration of the grignard reagent. These alkenyl sulfoxides were transformed into the corresponding -thio aldehydes in high yields via additive Pummerer rearrangement. (AU)

FAPESP's process: 11/11499-0 - Bioisosterism in the design of new antichagasic agents: integration of computational and experimental strategies
Grantee:Gustavo Henrique Goulart Trossini
Support type: Regular Research Grants
FAPESP's process: 13/20553-4 - Synthesis and functionalization of vinyl iodide sulfoxides
Grantee:Frederico Bernardes de Souza
Support type: Scholarships in Brazil - Doctorate (Direct)
FAPESP's process: 12/00424-2 - Synthesis of small libraries using potassium Organotrifluoroborates in Suzuki-Miyaura reactions
Grantee:Helio Alexandre Stefani
Support type: Research Projects - Thematic Grants