97807-82-4Relevant academic research and scientific papers
FACILE AMINOLYSIS OF EPOXIDES WITH DIETHYLALUMINUM AMIDES
Overman, Larry E.,Flippin, Lee A.
, p. 195 - 198 (1981)
Treatment of an epoxide with a diethylaluminum amide in dichloromethane at room temperature affords the corresponding β-amino alcohol in good yield.
Hydrogen Bonding Phase-Transfer Catalysis with Potassium Fluoride: Enantioselective Synthesis of β-Fluoroamines
Pupo, Gabriele,Vicini, Anna Chiara,Ascough, David M. H.,Ibba, Francesco,Christensen, Kirsten E.,Thompson, Amber L.,Brown, John M.,Paton, Robert S.,Gouverneur, Véronique
supporting information, p. 2878 - 2883 (2019/02/14)
Potassium fluoride (KF) is an ideal reagent for fluorination because it is safe, easy to handle and low-cost. However, poor solubility in organic solvents coupled with limited strategies to control its reactivity has discouraged its use for asymmetric C-F
Synthesis of 6-amino-3,5-deoxyinositol 1-phosphates via (1R,2R,4R,6S)- 1,6-epoxy-2,4-bis-benzyloxycyclohexane aminolysis in aqueous ytterbium triflate solution
Beaton, Martin,Gani, David
, p. 8549 - 8552 (2007/10/03)
(1R,2R,4R,6S)-1,6-Epoxy-2,4-bis-benzyloxycyclohexane was prepared from (-)-quinic acid and this, and cyclohexene oxide, were treated with various N- nucleophiles under a variety of conditions. In aqueous solution containing catalytic amounts of ytterbium (III) triflate, ammonia and alkylamines reacted smoothly to give the required trans-1,2-amino alcohols in quantitative recovery. Conversion of the 6-amino-2,4-bis-benzyloxycyclohexan- 1-ols to 6-amino-1,2,4-trihydroxycyclohexane 1-phosphates, probes for the mechanism of inositol monophosphatase, was achieved in good overall yield.
Ytterbium Triflate and High Pressure-mediated Ring Opening of Epoxides with Amines
Meguro, Masaki,Asao, Naoki,Yamamoto, Yoshinori
, p. 2597 - 2602 (2007/10/02)
Ring opening of epoxides with amines in THF takes place very readily in the presence of catalytic amounts of ytterbium triflate to give the corresponding β-amino alcohols in good to high yields.With tri- and tetra-substituted epoxides, the use of an excess (2 - 3 equiv.) of the amine is needed.The Yb(OTf)3-catalysed reaction of epoxides with amines in CH2Cl2 is quite complex; the yield of amino alcohols is generally lower and depends upon the addition order of the catalyst, amine and epoxide.The ring opening is accomplished also under high pressures in the absence of Yb(OTf)3.Ring opening with a combination of Yb(OTf)3 in CH2Cl2 and high pressure is more effective than the use, independently, of either Yb(OTf)3 or the high-pressure method.Oxetanes and β-lactones undergo ring opening in the presence of Yb(OTf)3.
Regio- and Stereo-selective Ring Opening of Epoxides with Amide Cuprate Reagents
Yamamoto, Yoshinori,Asao, Naoki,Meguro, Masaki,Tsukada, Naofumi,Nemoto, Hisao,et al.
, p. 1201 - 1203 (2007/10/02)
Amide cuprate reagents attack the less hindered carbon atom of epoxides to give 1,2-amino alcohols in good yields; this procedure is applied to the synthesis of an aziridine alcohol bearing a carborane framework which is a potentially useful 10B carrier for boron neutron capture therapy.
Kinetic Resolution of Racemic β-Hydroxy Amines by Enantioselective N-Oxide Formation
Miyano, Sotaro,Lu, Linda D.-L.,Viti, Steven M.,Sharpless, K. Barry
, p. 4350 - 4360 (2007/10/02)
A practical and fairly general procedure for the kinetic resolution of β-hydroxy tertiary amines is described.It involves the selective oxidation of one enantiomer to the N-oxide by using tert-butyl hydroperoxide (TBHP) and a chiral catalyst prepared by mixing 2 parts of titanium isopropoxide (Ti(O-i-Pr)4 and 1.2 parts of either (+)- or (-)-diisopropyl tartrate (DIPT).The product N-oxide and the unreacted amino alcohol are then easily separated by trituration or organic/aqueous solvent extractions, and chromatography is avoided.The oxidations are generally run to 60percent conversion and the results for 21 different amino alcohols are given.The enantiomeric excess of the slow reacting (i.e., recovered) enantiomer of the amino alcohol often exceeds 90percent.Among the more interesting substrates are the natural product ubine (95percent ee) (18), N-methylephedrine (95percent ee) (15), N-methylpseudoephedrine (93percent ee) (16), cis-2-(dimethylamino)cyclohexanol (>95percent ee) (13), trans-2-(dimethylamino)cyclohexanol (92percent ee) (12), N-benzylbevantolol (85percent ee) (27), and N-benzylpropranolol (32percent ee) (21).The latter two examples are β-blocker precursors.One of the most important characteristics of this new route to enantiomerically pure β-hydroxy amines is its predictability.Thus, in all cases examined to date, when using (+)-DIPT the absolute configuration at the carbinol center in the slow reacting enantiomer is always the same .A study of how the titanium/tartrate ratio, water, catalyst/substrate ratio, and temperature effect this reaction is discussed.
