286018-67-5

Upstream product

• 538-51-2 benzylidene phenylamine 
• 178424-96-9 (-)-(Z)-1-{(1S)-1-[1,1-dimethyl-1-(1,1,2-trimethylpropyl)silyl]-3-methylbutyl}-1-propenyl (1,1,1-trimethylsilyl) ether 

Relevant academic research and scientific papers

α-silyl controlled asymmetric Mannich reactions of acyclic ketones with imines

Enantiomerically pure α-dimethylthexylsilyl ketones (S)-1a-e were converted regio- and stereoselectively to the corresponding α-silylated trimethylsilyl enol ethers (Z,S)-2a-e. Stereoselective α-silyl controlled Mannich reactions with BF3·Et2O activated benzylideneaniline afforded the α'-silylated α,β-disubstituted β-amino ketones 3a-e in anti/syn ratios up to 80/20 and with moderate to good yields (61 - 82%). The major diastereomers (S,R,S)-3a-e (de ≥ 96%) were converted to the α,β-disubstituted β-amino ketones (R,S)-4a-e in excellent yields (92 - 96%), diastereomeric (de ≥ 96%) and enantiomeric excesses (ee = 95 - ≥ 99%) by removal of the silyl group with NH4F/n-Bu4NF.