(R)-2-Methyl-CBS-oxazaborolidine

(R)-2-Methyl-CBS-oxazaborolidine
Names
	IUPAC name (3aR)-1-Methyl-3,3-diphenyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole
	Other names (R)-Methyl oxazaborolidine; (R)-(+)-2-methyl-CBS-oxazaborolidine
Identifiers
CAS Number	112022-83-0
ChemSpider	8014210
Jmol 3D model	Interactive image
	InChI 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 Key: VCDGSBJCRYTLNU-AZWGFFAPSA-N ; InChI=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 Key: VCDGSBJCRYTLNU-AZWGFFAPBY ;
	SMILES O2B(N1CCC[C@@H]1C2(c3ccccc3)c4ccccc4)C ;
Properties
Chemical formula	C18H20BNO
Molar mass	277.17 g·mol−1
Appearance	Colorless to pale yellow liquid (in toluene)
Density	0.95 g/mL
Melting point	85 to 95 °C (185 to 203 °F; 358 to 368 K)
Boiling point	111 °C (232 °F; 384 K)
Vapor pressure	{{{value}}}
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

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(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.

References