19162-00-6Relevant articles and documents
High-speed microwave-promoted Mitsunobu inversions. Application toward the deracemization of sulcatol
Steinreiber, Andreas,Stadler, Alexander,Mayer, Sandra F,Faber, Kurt,Kappe
, p. 6283 - 6286 (2001)
An enantioconvergent synthesis of the aggregation pheromones (R)- and (S)-sulcatol (6-methyl-5-hepten-2-ol) is described. Key steps in the deracemization strategy are sequential combinations of enzymatic resolutions and Mitsunobu inversions. Racemization-
Enantioselective enzymatic resolution of racemic alcohols by lipases in green organic solvents
Belafriekh, Abderahmane,Secundo, Francesco,Serra, Stefano,Djeghaba, Zeineddine
, p. 473 - 478 (2017/03/23)
The effects of two eco-friendly solvents, 2-methyltetrahydrofuran (MeTHF) and cyclopentyl methyl ether (CPME), on the enzyme activity and enantioselectivity of Novozym 435, Candida rugosa lipase (CRL), Porcine pancreas lipase (PPL), Lipase AK, Lipase PS, and Lipozyme, a series of commercial lipases, in the enantioselective transesterfications of racemic menthol, racemic sulcatol and racemic α-cyclogeraniol were studied. Vinyl acetate was chosen as the acyl donor and the reactions were carried out at water activity 0.06. The activity of lipases in CPME was similar to that observed in other largely employed organic solvents [toluene and tert-butyl methyl ether (MTBE)], and was slightly lower in MeTHF. However, for most of the lipases tested, the enantioselectivity was higher in the eco-friendly solvents. Lipase AK exhibited a high enantioselectivity (E?=?232) for the resolution of racemic menthol but the reaction rate was low. Lipase formulation (the enzyme was frozen and lyophilized in potassium phosphate buffer without and with 5% (w/v) of sucrose, D-mannitol, or methoxy poly(ethylene glycol)) was tested with this lipase in order to improve its activity, which increased up to 4.5 times, compared to the untreated enzyme. CALB was found to be a useful biocatalyst for the resolution of racemic sulcatol, where high activity and enantioselectivity were obtained (E?≥?1000). For the resolution of the racemic primary alcohol α-cyclogeraniol, most of the lipases tested were active but not enantioselective, except lipase PS which displayed a moderate enantioselectivity (E?=?19). The effect of the presence of a low percentage of two ionic liquids (ILs) 1-Butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([BMIM][TFSI]) (5% (v/v)) and 1-Butyl-3-methylimidazoliumtetrafluoroborate ([BMIM][BF4]) (1% (v/v)) in the medium was also investigated. Only in the case of CRL the ILs slightly increased the enantioselectivity from E?=?91 to E?=?103 and E?=?120 for [BMIM][TFSI] and [BMIM][BF4], respectively. However, in all cases ILs caused a decrease of enzyme activity.
Odoriferous cyclic ethers via co-halogenation reaction: Facile preparation of nerol oxide, Florol, Florol methyl ether, and Pityol methyl ether
Gupta, Pankaj,Sethi, Vijay K.,Taneja, Subhash C.,Shah, Bhahwal A.,Andotra, Samar S.,Koul, Surrinder,Chimni, Swapandeep S.,Qazi, Ghulam N.
, p. 196 - 204 (2007/10/03)
A series of odoriferous cyclic ethers, including nerol oxide (1), Floral (2), Floral methyl ether (3), and Pityol methyl ether (4b), were prepared by a versatile synthetic protocol based on co-halogenation with 1,3-dibromo-5,5-dimethylhydantoin (= 1,3-dibromo-5,5-dimethylimidazolidine-2,4- dione; DDH) as the key step. The methodology provides a facile access to important perfumery molecules from abundantly available monoterpene alcohols.
