- Unexpected transfer hydrogenation of C-C-double bonds during Tandem-RCM-isomerization reactions
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Unexpected hydrogen transfer from 2-propanol to C-C-double bonds has been observed in the course of a Tandem RCM-isomerization reaction leading to sterically congested spirocycles.
- Schmidt, Bernd,Staude, Lucia
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Read Online
- Synthesis of tetrahydrofurans by cyclization of homoallylic alcohols with iodine/iodine(III)
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Tetrahydrofuran derivatives can be obtained by cyclofunctionalization of homoallylic alcohols bearing a terminal double bound by using [hydroxy(tosyloxy)iodo]benzene (HTIB, Kosers reagent) in the presence of a catalytic amount of I2 (20 mol %)
- Vasconcelos, Ramon S.,Silva Jr., Luiz F.,Giannis, Athanassios
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supporting information; experimental part
p. 1499 - 1502
(2011/05/06)
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- 3-Alkyl-p-menthan-3-ol derivatives: synthesis and evaluation of their physiological cooling activity
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Different 3-alkyl-p-methan-3-ol derivatives provide a strong physiological cooling effect with potential application as food and cosmetic additives. In order to investigate the influence of the chemical structure on the cooling sensation, the stereoselective syntheses of 29 different 3-alkyl-p-methan-3-ol derivatives were accomplished. All the compounds obtained are odorless and were evaluated by taste, considering two sensations: a cooling effect and bitterness. The results of this structure-activity relationship study highlight that compounds with a (1R,4S)-configuration are the isomers with the more intense cooling effect and lower bitterness. In addition, the structure of the 3-alkyl chain affected the latter properties. Increasing the chain length over two carbon atoms does not change the cooling power, but enhances the bitterness with the additional feature that the branched isomers are considerably more bitter than the linear ones. Overall, the 3-alkyl-p-menthan-3-ol isomers with the best quality in terms of high cooling power and low bitterness are (1R,4S)-3-(hydroxymethyl)-p-menthan-3-ol diastereoisomers (-)-38 and (-)-42.
- Fuganti, Claudio,Joulain, Daniel,Maggioni, Francesco,Malpezzi, Luciana,Serra, Stefano,Vecchione, Andrea
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experimental part
p. 2425 - 2437
(2009/04/06)
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