Hydrochloric Acid → (3R)-1-phenyl-hex-5-en-3-ol
Reaction equation
[CH2:1]([Si]1(OC(C)C)N(C)[C@@H](C)[C@H](C2C=CC=CC=2)O1)[CH:2]=[CH2:3].[CH:21](=[O:30])[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl.CCOC(C)=O>C1(C)C=CC=CC=1>[C:24]1([CH2:23][CH2:22][C@@H:21]([OH:30])[CH2:3][CH:2]=[CH2:1])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1Participants
Conditions
- Temperature
- 21 °C
Procedure
Enantioselective allylation of dihydrocinnamaldehyde to give (3R)-1-phenyl-hex-5-en-3-ol: To a solution of (4S,5S)-2-Allyl-2-isopropoxy-3,4-dimethyl-5-phenyl-[1,3,2]oxazasilolidine (0.437 g, 1.5 mmol) in toluene (2.5 mL) was added dihydrocinnamaldehyde (0.132 mL, 1.0 mmol). The mixture was allowed to stir at ambient temperature (˜21° C.) for 18 hours. To this solution was added 1N HCl (4 mL) and EtOAc (4 mL) and the mixture was stirred for 10 min. The layers were separated and the aqueous layer was extracted with EtOAc (3×5 mL). The combined organics were dried over MgSO4, filtered, and concentrated. The residue was purified by chromatography on silica gel (5% EtOAc/hexanes) to afford 0.119 g (69%) of (3R)-1-phenyl-hex-5-en-3-ol in 94% enantiomeric excess (ee).
Workup
- stirringthe mixture was stirred for 10 min
- customThe layers were separated
- extractionthe aqueous layer was extracted with EtOAc (3×5 mL)
- dry with materialThe combined organics were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by chromatography on silica gel (5% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-4b8f7ea544b440cab756c1c6bb4725d2
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07534905B2
Reaction notes
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