53723-50-5Relevant academic research and scientific papers
Lipase-catalyzed kinetic resolution of 2-methylene-substituted cycloalkanols in batch and continuous-flow modes
Tomin, Anna,Hornyánszky, Gábor,Kupai, Katalin,Dorkó, Zsanett,ürge, László,Darvas, Ferenc,Poppe, László
experimental part, p. 859 - 865 (2011/12/15)
Kinetic resolutions of cyclic racemic secondary alcohols (2-methylenecyclopentan-1-ol rac-1a, 2-methylenecyclohexan-1-ol rac-1b, 2-methylenecycloheptan-1-ol rac-1c, 6-methylene-[1,3]dioxepan-5-ol rac-1d, 2,2-dimethyl-6-methylene-[1,3]dioxepan-5-ol rac-1e and trans-2-bromocyclohexan-1-ol rac-3) catalyzed by different (commercial and in-house-made) lipases were performed using vinyl acetate in THF-hexane. In the most typical cases (rac-1b, rac-1d and rac-3), the immobilized Candida antarctica lipase B (CaLB, for rac-1b and rac-3)- or sol-gel immobilized Pseudomonas fluorescens lipase (sol-gel LAK, for rac-1d)-catalyzed batch mode reactions were compared to the continuous mode reactions carried out in an enzyme-filled stainless steel bioreactor. The effect of temperature (20-60 °C) and flow rate (0.1-0.3 ml min-1) on the continuous-flow acetylation of rac-1b, rac-1d and rac-3 were investigated. In the kinetic resolutions of rac-1b, rac-1d and rac-3, the enantiomeric selectivities (E) were similar in the continuous-flow and batch (shake flask) modes. However, the productivities (specific reaction rate: r), were significantly higher in the continuous-flow mode biotransformations of rac-1b, rac-1d and rac-3.
Preparation of Allylic Acetates from Simple Alkenes by Palladium(II)-Catalyzed Acetoxylation
Hansson, Sverker,Heumann, Andreas,Rein, Tobias,Akermark, Bjoern
, p. 975 - 984 (2007/10/02)
The scope and limitations of palladium-catalyzed allylic acetoxylation has been investigated, using benzoquinone-manganese dioxide as the reoxidation system.Unsubstituted cycloalkenes gave good to excellent yields of allylic acetates.Total yields were also good for many substituted cycloalkenes and for linear alkenes, but these substrates generally gave several isomeric acetates.The exploratory mechanistic studies show that the acetoxylation can proceed via both 1,2-acetoxypalladation and η3-allylpalladium complex formation.The keen balance between these processes depends on the structure of the alkene.
THE NITROGENATED ALLYLIC SYSTEM AS AN INTRAMOLECULAR NUCLEOPHILE: A NEW ROUTE TO PYRAZOLES
Momose, Takefumi,Toyooka, Naoki,Ikuta, Takashi,Yanagino, Hironobu
, p. 789 - 793 (2007/10/02)
A new route to pyrazoles via the cyclization of N-allyl-N-nitrosoamides is described.
Silicon-based nucleophile mediated one-carbon ring expansion reaction of 1-(trimethylsilylmethyl)cycloalkanecarbaldehydes
Tanino,Sato,Kuwajima
, p. 6551 - 6554 (2007/10/02)
Under the influence of an appropriate Lewis acid, TMS sulfide and TMS-OTf induced one carbon ring expansion of 1-(trimethylsilylmethyl)cycloalkanecarbaldehydes to afford the corresponding 2-methylenecycloalkyl sulfides and ethers, or their isomerized ones
The conformational preference of methoxyl and acetoxyl groups in 3-oxycyclohexenes, 2-oxymethylenecyclohexanes, and 1-oxytetralins and the generalized anomeric effect
Ouedraogo, Adama,Viet, Minh Tan Phan,Saunders, John K.,Lessard, Jean
, p. 1761 - 1768 (2007/10/02)
The 13C and 1H nuclear magnetic resonance data of 3-oxycyclohexenes, 2-oxymethylenecyclohexanes, and 1-oxytetralins show (i) that the pseudoaxial preference is larger for the acetoxyl group than for the methoxyl group in 3-oxycyclohexenes, (ii) that the m
Anti-Markovnikov Addition of Nucleophiles to a Non-conjugated Olefin via Single Electron Transfer Photochemistry
Gassman, Paul G.,Bottorff, Kyle J.
, p. 5449 - 5452 (2007/10/02)
Nucleophilic solvent has been added regiospecifically in an anti-Markovnikov manner to a simple non-conjugated olefin, 1-methylcyclohexene, through single electron transfer induced photochemistry using the 1-cyanonaphthalene - biphenyl pair for achieving photooxidation.
STEREOCHEMICAL STUDIES-XXVIII. CONFORMATIONAL EQUILIBRIA OF 2-OCH3, 2-OCOCH3 AND 2-Br DERIVATIVES OF ω-SUBSTITUTED METHYLENECYCLOHEXANES
Zefirov, N. S.,Baranenkov, I. V.
, p. 1769 - 1776 (2007/10/02)
The conformational equilibria of the titled compounds, 10-13, have been determined by 1H NMR and analysed in terms of steric (A(1,3) repulsion, 15) and electronic effects.The conformational equilibria of OMe and Br derivatives depend
