(R)-2-Methyl-CBS-oxazaborolidine

changed changed 477343124 (R)-2-Methyl-CBS-oxazaborolidine (R)-2-Methyl-CBS-oxazaborolidine.svg (3aR)-1-Methyl-3,3-diphenyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole (R)-Methyl oxazaborolidine; (R)-(+)-2-methyl-CBS-oxazaborolidine correct chemspider 8014210 9838490 601-151-0 VCDGSBJCRYTLNU-AZWGFFAPBY correct chemspider 1S/C18H20BNO/c1-19-20-14-8-13-17(20)18(21-19,15-9-4-2-5-10-15)16-11-6-3-7-12-16/h2-7,9-12,17H,8,13-14H2,1H3/t17-/m1/s1 changed chemspider VCDGSBJCRYTLNU-AZWGFFAPSA-N changed ?? 112022-83-0 correct FDA 4WZ68942D5 O2B(N1CCC[C@@H]1C2(c3ccccc3)c4ccccc4)C 1/C18H20BNO/c1-19-20-14-8-13-17(20)18(21-19,15-9-4-2-5-10-15)16-11-6-3-7-12-16/h2-7,9-12,17H,8,13-14H2,1H3/t17-/m1/s1 18 20 1 1 1 Colorless to pale yellow liquid (in toluene) 0.95 g/mL 85 to 95 111 (R)-2-Methyl-CBS-oxazaborolidine https://pubchem.ncbi.nlm.nih.gov/compound/9838490#section=GHS-Classification pubchem.ncbi.nlm.nih.gov 05 07 Danger H302 H318 P264 P264+P265 P270 P280 P301+P317 P305+P354+P338 P317 P330 P501 (R)-2-Methyl-CBS-oxazaborolidine is an organoboron catalyst that is used in organic synthesis. This catalyst, developed by Shinichi ItsunoHirao, A. Itsuno, S. Nakahama, S. Yamazaki, N. J. Chem. Soc. Chem. Commun. Asymmetric reduction of aromatic ketones with chiral alkoxy-amineborane complexes 1981 7 315–317 10.1039/C39810000315Itsuno, S. Nakano, M. Miyazaki, K. Masuda, H. Ito, K. Hirao, A. Nakahama, S. J. Chem. Soc. Perkin Trans. 1 1985 2039–2044 10.1039/p19850002039 Asymmetric synthesis using chirally modified borohydrides. Part 3. Enantioselective reduction of ketones and oxime ethers with reagents prepared from borane and chiral amino alcohols and Elias James Corey,Corey, E. J. Bakshi, R. K. Shibata, S. J. Am. Chem. Soc. 1987 109 5551–5553 10.1021/ja00252a056 Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines. Mechanism and synthetic implications 18 1987JAChS.109.5551C Corey, E. J. Bakshi, R. K. Shibata, S. Chen, C.-P. Singh, V. K. J. Am. Chem. Soc. 1987 109 7925–7926 10.1021/ja00259a075 A stable and easily prepared catalyst for the enantioselective reduction of ketones. Applications to multistep syntheses 25 1987JAChS.109.7925C Corey, E. J. Azimioara, M. Sarshar, S. Tetrahedron Lett. 1992 33 3429–3430 10.1016/S0040-4039(00)92654-6 X-Ray crystal structure of a chiral oxazaborolidine catalyst for enantioselective carbonyl reduction 24 97345807 is generated by heating (R)-(+)-2-(diphenylhydroxymethyl) pyrrolidine along with trimethylboroxine or methylboronic acid. It is an excellent tool for the synthesis of alcohols in high enantiomeric ratio. Generally, 2-10 mol% of this catalyst is used along with borane-tetrahydrofuran (THF), borane-dimethylsulfide, borane-N,N-diethylaniline, or diborane as the borane source. Enantioselective reduction using chiral oxazaborolidine catalysts has been used in the synthesis of commercial drugs such as ezetimibe and aprepitant. See also CBS catalyst Corey-Itsuno reduction References Category:Organoboron compounds Category:Reagents for organic chemistry Category:Catalysts Category:Phenyl compounds Category:Pyrrolidines