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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 some fenchyl-substituted alkenes and enol-ethers containing 3-oxyphenyl substituents by the Barton-Kellogg reaction

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Author(s):
Ciscato, Luiz Francisco M. L. [1, 2] ; Bastos, Erick L. [3] ; Bartoloni, Fernando H. [1] ; Guenther, Wolfgang [2] ; Weiss, Dieter [2] ; Beckert, Rainer [2] ; Baader, Wilhelm Josef [1]
Total Authors: 7
Affiliation:
[1] Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, BR-05508000 Sao Paulo - Brazil
[2] Univ Jena, Inst Organ Chem & Makromol Chem, D-07737 Jena - Germany
[3] Univ Fed ABC, Ctr Ciencias Nat & Humanas, BR-09210170 Santo Andre, SP - Brazil
Total Affiliations: 3
Document type: Journal article
Source: Journal of the Brazilian Chemical Society; v. 21, n. 10, p. 1896-1904, 2010.
Web of Science Citations: 5
Abstract

The synthesis of one fenchyl-substituted alkene and two enol-ethers, containing 3-oxyphenyl substituents by the Barton-Kellogg reaction is described. The tri-substituted aromatic fenchyl-alkene 1a was prepared in 53% yield from thiofenchone and a diazoanisole; whereas enol-ethers 1b and 1c were obtained (95 and 75% yield, respectively) using an inverse approach based on diazofenchone and aromatic thionoesters. A mixture of Z and E isomers was obtained in all cases; isomer attribution and quantification has been carried out by analysis of NMR spectroscopic data assisted by theoretical calculations (E/Z ratio: 1a = 0.72, 1b = 2.2, 1c = 1.8). Reaction proceeds with low stereoselectivity leading to the preferential formation of diastereoisomeric olefins and enol-ethers where the aromatic substituent resides at the side of the two fenchyl methyl groups. (AU)

FAPESP's process: 07/00684-6 - Synthesis and application of modified flower pigments
Grantee:Erick Leite Bastos
Support Opportunities: Research Grants - Young Investigators Grants