Hydrochloric Acid → (3R)-1-phenyl-hex-5-en-3-ol
Reaction equation
[CH2:1]([Si]1(Cl)N(C)[C@@H](C)[C@H](C2C=CC=CC=2)O1)[CH:2]=[CH2:3].[CH:18](=[O:27])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl.CCOC(C)=O>C1(C)C=CC=CC=1>[C:21]1([CH2:20][CH2:19][C@@H:18]([OH:27])[CH2:3][CH:2]=[CH2:1])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1Participants
Conditions
- Temperature
- -10 °C
Procedure
Enantioselective allylation of dihydrocinnamaldehyde to give (3R)-1-phenyl-hex-5-en-3-ol: To a cooled (−10° C.) solution of (4S,5S)-2-Allyl-2-chloro-3,4-dimethyl-5-phenyl-[1,3,2]oxazasilolidine (380 mg, 1.5 mmol) in toluene (5 mL) was added dihydrocinnamaldehyde (1.0 mmol). The reaction mixture was maintained at −10° C. for 2 h. To this cooled solution was added 1N HCl (4 mL) and EtOAc (4 mL) and the mixture was vigorously stirred for 15 min. The layers were separated and the aqueous layer was extracted with EtOAc (2×5 mL). The combined organics were dried (MgSO4), filtered, and concentrated. The residue was purified by flash chromatography on silica gel to give (3R)-1-phenyl-hex-5-en-3-ol in 84% yield and 88% enantiomeric excess (ee).
Workup
- customThe layers were separated
- extractionthe aqueous layer was extracted with EtOAc (2×5 mL)
- dry with materialThe combined organics were dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash chromatography on silica gel
Sources & evidence
- ORD record
- ord-aa8b17404072423bbb4374dfb33f22cc
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07534905B2
Reaction notes
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