Isopropanol → Et2AlCN i-PrOH
Reaction equation
C([Al])C.[CH:4]([OH:7])([CH3:6])[CH3:5].[C-:8]#[N:9].[CH2:10]([Al+:12][CH2:13][CH3:14])[CH3:11]>C1COCC1>[Al:12]([C:8]#[N:9])([CH2:13][CH3:14])[CH2:10][CH3:11].[CH3:5][CH:4]([OH:7])[CH3:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The sulfinimine-mediated asymmetric synthesis involves addition of ethylaluminium cyanoisopropoxide generated in situ by addition of isopropanol (i-PrOH) to diethylaluminium cyanide (Et2AlCN) to the compound VIIa. Thus treatment of compound VIIa (1.0 mmol) at −78° C. in THF with 1.5/1.0 equiv of Et2AlCN/i-PrOH gave amino nitrile VIII in good yield (50-70%).
Workup
- customThe sulfinimine-mediated asymmetric synthesis
Sources & evidence
- ORD record
- ord-868c36ae70b54fae9b68367883f5729d
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08748631B2
Reaction notes
Loading…