^Hirao, A.; Itsuno, S.; Nakahama, S.; Yamazaki, N. (1981). "Asymmetric reduction of aromatic ketones with chiral alkoxy-amineborane complexes". J. Chem. Soc. Chem. Commun. (7): 315–317. doi:10.1039/C39810000315.
^Itsuno, S.; Nakano,M.; Miyazaki, K.; Masuda, H.; Ito, K.; Hirao, A.; Nakahama, S. (1985). "Asymmetric synthesis using chirally modified borohydrides. Part 3. Enantioselective reduction of ketones and oxime ethers with reagents prepared from borane and chiral amino alcohols". J. Chem. Soc. Perkin Trans. 1: 2039–2044. doi:10.1039/p19850002039.
^Corey, E. J.; Bakshi, R. K.; Shibata, S. (1987). "Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines. Mechanism and synthetic implications". J. Am. Chem. Soc.109 (18): 5551–5553. doi:10.1021/ja00252a056.
^Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C.-P.; Singh, V. K. (1987). "A stable and easily prepared catalyst for the enantioselective reduction of ketones. Applications to multistep syntheses". J. Am. Chem. Soc. 109 (25): 7925–7926. doi:10.1021/ja00259a075.
^Corey, E. J.; Azimioara,M.; Sarshar, S. (1992). "X-Ray crystal structure of a chiral oxazaborolidine catalyst for enantioselective carbonyl reduction". Tetrahedron Lett.33 (24): 3429–3430. doi:10.1016/S0040-4039(00)92654-6. S2CID 97345807.
April 09, 2024
methyl, oxazaborolidine, organoboron, catalyst, that, used, organic, synthesis, this, catalyst, developed, itsuno, elias, james, corey, generated, heating, diphenylhydroxymethyl, pyrrolidine, along, with, trimethylboroxine, methylboronic, acid, excellent, tool. R 2 Methyl CBS oxazaborolidine is an organoboron catalyst that is used in organic synthesis This catalyst developed by Itsuno 1 2 and Elias James Corey 3 4 5 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 R 2 Methyl CBS oxazaborolidine NamesPreferred IUPAC name 3aR 1 Methyl 3 3 diphenyltetrahydro 1H 3H pyrrolo 1 2 c 1 3 2 oxazaboroleOther names R Methyl oxazaborolidine R 2 methyl CBS oxazaborolidineIdentifiersCAS Number 112022 83 0 N3D model JSmol Interactive imageChemSpider 8014210 YECHA InfoCard 100 103 901EC Number 601 151 0PubChem CID 9838490CompTox Dashboard EPA DTXSID40920652InChI InChI 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 YKey VCDGSBJCRYTLNU AZWGFFAPSA N NInChI 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 s1Key VCDGSBJCRYTLNU AZWGFFAPBYSMILES O2B N1CCC C H 1C2 c3ccccc3 c4ccccc4 CPropertiesChemical formula C 18H 20B N OMolar mass 277 17 g mol 1Appearance Colorless to pale yellow liquid in toluene Density 0 95 g mLMelting point 85 to 95 C 185 to 203 F 358 to 368 K Boiling point 111 C 232 F 384 K HazardsGHS labelling PictogramsSignal word DangerHazard statements H224 H225 H302 H304 H315 H318 H319 H332 H335 H336 H361 H373Precautionary statements P201 P202 P210 P233 P240 P241 P242 P243 P260 P261 P264 P270 P271 P280 P281 P301 P310 P301 P312 P302 P352 P303 P361 P353 P304 P312 P304 P340 P305 P351 P338 P308 P313 P310 P312 P314 P321 P330 P331 P332 P313 P337 P313 P362 P370 P378 P403 P233 P403 P235 P405 P501Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox referencesSee also editCBS catalyst Corey Itsuno reductionReferences edit Hirao A Itsuno S Nakahama S Yamazaki N 1981 Asymmetric reduction of aromatic ketones with chiral alkoxy amineborane complexes J Chem Soc Chem Commun 7 315 317 doi 10 1039 C39810000315 Itsuno S Nakano M Miyazaki K Masuda H Ito K Hirao A Nakahama S 1985 Asymmetric synthesis using chirally modified borohydrides Part 3 Enantioselective reduction of ketones and oxime ethers with reagents prepared from borane and chiral amino alcohols J Chem Soc Perkin Trans 1 2039 2044 doi 10 1039 p19850002039 Corey E J Bakshi R K Shibata S 1987 Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines Mechanism and synthetic implications J Am Chem Soc 109 18 5551 5553 doi 10 1021 ja00252a056 Corey E J Bakshi R K Shibata S Chen C P Singh V K 1987 A stable and easily prepared catalyst for the enantioselective reduction of ketones Applications to multistep syntheses J Am Chem Soc 109 25 7925 7926 doi 10 1021 ja00259a075 Corey E J Azimioara M Sarshar S 1992 X Ray crystal structure of a chiral oxazaborolidine catalyst for enantioselective carbonyl reduction Tetrahedron Lett 33 24 3429 3430 doi 10 1016 S0040 4039 00 92654 6 S2CID 97345807 Retrieved from https en wikipedia org w index php title R 2 Methyl CBS oxazaborolidine amp oldid 1194902084, wikipedia, wiki, book, books, library,
