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(R)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine
(CAS RN:112022-83-0 Product Number:D2130)

Structure

(R)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine
Synonym (R)-3,3-Diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole
Synonym (R)-Me-CBS Catalyst

General Information

Product Number D2130

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Purity/Analysis Method >97.0%(T)
Storage Temperature
M.F. / M.W. C18H20BNO=277.17
CAS RN 112022-83-0
Related CAS RN
MDL Number MFCD00078440
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Specification

Appearance White to Almost white powder to crystal
Purity(Nonaqueous Titration) min. 97.0 %
Specific rotation [a]20/D +66.0 to +73.0 deg(C=1, MeOH)

References

Reaxys-RN 9059874
PubChem SID 87568574

Transport Information

HS Number 2934999090

Application

Asymmetric Reduction Using CBS Catalyst

Experimental procedure5): To a solution of 1 (3.52 g, 10.8 mmol) in toluene (85 mL) is added (R)-CBS-Me catalyst (1 mol/L in toluene, 4.30 mL, 4.30 mmol) and the solution is cooled to -78 °C. A solution of catecholborane (3.44 mL, 32.3 mmol) in toluene (20 mL) is added dropwise over 30 minutes. After stirring for 6 hours at -78 °C, water (40 mL) is added and the reaction is allowed to warm to rt. The reaction mixture is poured on water (150 mL) and extracted with Et2O (3 x 125 mL). The combined organic layers are washed with 1 mol/L NaOH (2 x 100 mL), saturated NaCl (100 mL), dried over MgSO4, and concentrated under vacuum. The crude product is purified by flash chromatography (hexanes:EtOAc = 4:1) to provide 3.00 g (85% yield, 98% ee) of 2 as a clear oil.

References

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