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CAS RN: 112022-83-0 | Product Number: D2130
(R)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine
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Purity: >97.0%(T)
Synonyms:
- (R)-3,3-Diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole
- (R)-Me-CBS Catalyst
- (R)-(+)-2-Methyl-CBS-oxazaborolidine
Product Documents:
| Size | Unit Price | Same Day | 2-3 Business Days | Other Lead Time |
Shipping Information
|
|---|---|---|---|---|---|
| 1G |
$67.00
|
10 | 0 | Contact Us | |
| 5G |
$222.00
|
8 | 0 | Contact Us |
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| Product Number | D2130 |
| Purity / Analysis Method | >97.0%(T) |
| Molecular Formula / Molecular Weight | C__1__8H__2__0BNO = 277.17 |
| Physical State (20 deg.C) | Solid |
| Storage Temperature | Frozen (<0°C) |
| Store Under Inert Gas | Store under inert gas |
| Condition to Avoid | Moisture Sensitive,Heat Sensitive |
| Packaging and Container | 1G-Glass Bottle with Plastic Insert (View image) |
| CAS RN | 112022-83-0 |
| Reaxys Registry Number | 9059874 |
| PubChem Substance ID | 87568574 |
| MDL Number | MFCD00078440 |
Specifications
| Appearance | White to Almost white powder to crystal |
| Purity(Nonaqueous Titration) | min. 97.0 % |
| Specific rotation [a]20/D | +68.0 to +75.0 deg(C=1, MeOH) |
| NMR | confirm to structure |
Properties (reference)
| Specific Rotation | 68° (C=1,MeOH) |
GHS
Related Laws:
Transport Information:
| H.S.code* | 2934.99-000 |
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
- 1)Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines. Mechanism and synthetic implications
- 2)A stable and easily prepared catalyst for the enantioselective reduction of ketones. Applications to multistep syntheses
- 3)Enantioselective route to a key intermediate in the total synthesis of ginkgolide B
- 4)Total synthesis of (±)-forskolin
- 5)Total Synthesis of (+)-Lyconadin A and Related Compounds via Oxidative C－N Bond Formation
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Related Products
(R)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine (ca. 1mol/L in Toluene)
| Product # | D5911 |
| CAS RN | 112022-83-0 |
| Purity / Analysis Method: |