134070-85-2Relevant academic research and scientific papers
Enzymatic resolution of (±)-cis-2-aminocyclopentanol and (±)-cis-2- aminocyclohexanol
Luna, Amparo,Astorga, Covadonga,Fueloep, Ferenc,Gotor, Vicente
, p. 4483 - 4487 (1998)
(±)-cis-N-Benzyloxycarbonyl-2-aminocyclopentanol was efficiently resolved by O-acylation with Pseudomonas cepacia lipase, as was (±)-cis-N- benzyloxycarbonyl-2-aminocyclohexanol when Candida antarctica lipase was used.
New procedure for the preparation of (1 R,2 R)-2-[(R)-3-(benzyloxy)pyr- rolidin-1-yl]cyclohexanol
Ye, Haiwei,Yu, Chuanming,Zhong, Weihui
, p. 51 - 56 (2012/04/10)
A novel route to an intermediate of vernakalant, (1R,2R)-2-[(R)-3- (benzyloxy)pyrrolidin-1-yl]cyclohexanol from ethyl (R)-4-chloro-3- hydroxybutanoate is described. It was found that the key intermediate (R)-4-(benzyloxy)-1-[(1R,2R)-2-(tert-butyldimethylsiloxy)cyclohexyl] pyrrolidin-2-one could be isolated with high dia-stereomeric excess (up to 99% de) from its isomer by column chromatography alone, without further chemical resolution. Georg Thieme Verlag Stuttgart. New York.
Alkyl 4-chlorobenzoyloxycarbamates as highly effective nitrogen source reagents for the base-free, intermolecular aminohydroxylation reaction
Harris, Lawrence,Mee, Simon P. H.,Furneaux, Richard H.,Gainsford, Graeme J.,Luxenburger, Andreas
experimental part, p. 358 - 372 (2011/04/17)
Ethyl-(7), benzyl-(8), tert-butyl-(9), and fluorenylmethyl-4- chlorobenzoyloxycarbamates (10) have been prepared as storable and easy-to-prepare nitrogen sources for use in the intermolecular Sharpless aminohydroxylation reaction and its asymmetric variant. These reagents were found to be effective under base-free reaction conditions. The scope and limitations of these methods have been explored using a variety of alkenes, among which, trans-cinnamates, in particular, proved to be good substrates.
IMPROVED AMINOHYDROXYLATION OF ALKENES
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Page/Page column 52, (2012/01/06)
The invention relates to a process for the aminohydroxylation of alkenes using N-oxycarbamate reagents, e.g. N-acyloxycarbamate, N-alkyloxycarbonyloxycarbamate and N-aralkoxycarbonyloxycarbamate reagents. The invention particularly relates to an intermolecular aminohydroxylation reaction that can be carried out in the absence of added base. The invention also relates to novel N-oxycarbamate reagents that are stable crystalline materials. The process of the invention is useful in the synthesis of compounds having a vicinal amino alcohol moiety, such as biologically active compounds.
A General Route to the Synthesis of N-Protected 1-Substituted and 1,2-Disubstituted Taurines
Xu, Jiaxi,Xu, Shu
, p. 276 - 282 (2007/10/03)
N-Benzyloxycarbonyl protected α-substituted and αβ- disubstituted taurines were synthesized from olefins and epoxides via N-benzyloxycarbonylamino alcohol thioacetates as key intermediates. They are important sulfur analogues of naturally occurring amino acids and building blocks for the synthesis of α-substituted and α,β- disubstituted β-sulfonopeptides.
Enzymatic resolution of (±)-trans-2-aminocyclohexanol and (±) trans-2-aminocyclopentanol
Maestro, Alicia,Astorga, Covadonga,Gotor, Vicente
, p. 3153 - 3159 (2007/10/03)
Candida antarctica lipase (CAL) catalyzes the resolution of (±)-trans-2-aminocyclohexanol by alkoxycarbonylation or acylation reactions. Besides, N-benzyloxycarbonyl derivatives of (±)-trans-2-aminocyclohexanol and (±)-trans-2-aminocyclopentanol are efficiently resolved through O-acylation by Pseudomonas cepacia lipase (PSL).
Preparation of 2-oxazolidinones by intramolecular nucleophilic substitution
Van Delft, Floris L.,Timmers, Cornelis M.,Van Der Marel, Gijs A.,Van Boom, Jacques H.
, p. 450 - 454 (2007/10/03)
Treatment of N-alkoxycarbonyl, N-benzyl protected β-amino alcohols with triphenylphosphine and hexachloroethane in 1,2-dichloroethane induces cyclization to 2-oxazolidinones, which are formed by intramolecular attack with inversion of configuration at the secondary alcohol. In contrast, mono N-substituted alkyl carbamates undergo chlorination under the same conditions.
