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Synthesis of 1,2-amino alcohols having tertiary acohol moietry

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2006
Sümer, Burak
An applicable method for the racemic synthesis of 1,2-amino alcohols having tertiary alcohol moiety was developed. This method can be used as a general method for the synthesis of various 1,2-amino alcohols with various tertiary alcohol moieties by changing chloroacetone with different monohalo ketones, and with different aryl halides or alkyl halides. The resultant racemic 1,2-aminoe alcohols were tried to resolve by using various hydrolase type enzymes under different conditions by changing the parameters i.e. solvent, temperature and substrate: enzyme ratios. Finally, poorly resolved amino alcohol 20 with 21 % was used as chiral ligand in diethyl zinc reaction to benzaldhyde and afforded (R)-1-phenylpropan-1-ol almost with 21 % e.e..