108267-20-5Relevant articles and documents
Synthesis and crystal structure of perhydro-1,4-benzoxazino[2,3-n]phenoxazine
Kl?ui, Wolfgang,Schoger, Susanne,Nieger, Martin
, p. 801 - 804 (1997)
The oxidation of trans-2-aminocyclohexanol with nitrobenzene in the presence of catalytic amounts of iron inter alia yields perhydro-1,4-benzoxazino[2,3-n]phenoxazine (1). This compound has been characterized analytically, spectroscopically and by X-ray diffraction. It is postulated that the oxidation of the 2-aminoalcohol leads to the intermediate formation of a 1,2-dione. The direct synthesis of 1 from trans-2-aminocyclohexanol and 1,2-cyclohexandione supports this hypothesis.
A NOVEL AND EFFICIENT SYNTHESIS OF (+)- AND (-)-TRANS-2-AMINOCYCLOHEXANOL BY ENZYMATIC HYDROLYSIS
Faber, Kurt,Hoenig, Helmut,Seufer-Wasserthal, Peter
, p. 1903 - 1904 (1988)
Both enantiomers of trans-2-aminocyclohexanol were obtained by enzimatic hydrolysis of (+/-)-2-azidocyclohexanoates using lipases and subsequent hydrogenation.
Cobalt(II) chloride-catalyzed chemoselective sodium borohydride reduction of azides in water
Fringuelli, Francesco,Pizzo, Ferdinando,Vaccaro, Luigi
, p. 646 - 650 (2000)
Reduction of azides to amines and amides was carried out with NaBH4/CoCl2·6H2O in sole water at 25 °C under catalytic heterogeneous conditions. A broad spectrum of azides was reduced in a short time, chemoselectively in high yield and purity.
Resolution of β-aminoalcohols and 1,2-diamines using fractional crystallization of diastereomeric salts of dehydroabietic acid
Guangyou, Zhang,Yuquing, Liao,Zhaohui, Wang,Nohira, Hiroyuki,Hirose, Takuji
, p. 3297 - 3300 (2003)
(S)-(+)-1-Amino-3-phenyloxy-2-propanol, (R)-(-)-2-amino-1-phenylethanol, (S)-(+)-1-amino-2-propanol, (1S,2S)-(+)-2-aminocyclohexanol and (1S,2S)-(+)-1,2-diaminocyclohexane were resolved using dehydroabietic acid. It was shown that good to high enantiomeric purity, between 81～>99% ee, was obtained and that dehydroabietic acid could be easily and efficiently recovered in a reusable form.
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Winstein,Boschan
, p. 4669,4677 (1950)
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Enzymatic method of preparation of opticallly active trans-2-amino cyclohexanol derivatives
Ursini,Maragni,Bismara,Tamburini
, p. 1369 - 1377 (1999)
Supported Lipase Amano PS-D catalyzes the resolution of (±)-trans-2- tert butoxycarbonyl amino cyclohexanol by a selective acylation reaction. Using the supported enzyme gave a much faster reaction compared to existing methodology on similar substrates. A variety of acylating agents were investigated, with vinyl acetate providing the most practical and convenient procedure.
Hybrid Organo- and Biocatalytic Process for the Asymmetric Transformation of Alcohols into Amines in Aqueous Medium
Liardo, Elisa,Ríos-Lombardía, Nicolás,Morís, Francisco,Rebolledo, Francisca,González-Sabín, Javier
, p. 4768 - 4774 (2017/07/24)
A hybrid organo- and biocatalytic system for the asymmetric conversion of racemic alcohols into amines was developed. Combining an organocatalyst, AZADO, an oxidant, NaOCl, and an enzyme, ω-transaminase, we implemented a one-pot oxidation-transamination sequential process in aqueous medium. The method showed broad substrate scope and was successfully applied to conventional secondary alcohols and sterically hindered β-substituted cycloalkanols, where a highly stereoselective dynamic asymmetric bioamination enabled us to set up both contiguous stereocenters with very high enantio- and diastereomeric ratio (>90% yield, >99% ee, and up to 49:1 dr).
