(R)-2-Methyl-CBS-oxazaborolidine

(R)-2-Methyl-CBS-oxazaborolidine
Names
	Preferred IUPAC name (3aR)-1-Methyl-3,3-diphenyltetrahydro-1H,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 ;
3D model (JSmol)	Interactive image;
ChemSpider	8014210 ;
ECHA InfoCard	100.103.901
EC Number	601-151-0;
PubChem CID	9838490;
CompTox Dashboard (EPA)	DTXSID40920652 ;
	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 gÂ·molâ1
Appearance	Colorless to pale yellow liquid (in toluene)
Density	0.95 g/mL
Melting point	85 to 95 Â°C (185 to 203 Â°F; 358 to 368 K)
Boiling point	111 Â°C (232 Â°F; 384 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H318
Precautionary statements	P264, P264+P265, P270, P280, P301+P317, P305+P354+P338, P317, P330, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa). verify (what is ?) Infobox references

(R)-2-Methyl-CBS-oxazaborolidine is an organoboron catalyst that is used in organic synthesis. This catalyst, developed by Shinichi Itsuno^[2]^[3] and Elias James Corey,^[4]^[5]^[6] 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.

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