Nitromethane → HCID 10012389, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, 159 mg (0.56 mmol) of (S)-2,2'-dihydroxy-1,1'-binaphthyl were added to 7.56 cm3 of a THF solution of lanthanum tri-t-butoxide (4.9×10-2 mol.dm-3 as a monomer) at room temperature, followed by stirring for 2 hours. In the presence of 10 mol % (based on La) of the resultant solution, 2 mol equivalents (based on La) of LiCl and 10 mol equivalents (based on La) water, cyclohexylaldehyde reacted with nitromethane (10 equivalents) in tetrahydrofuran at -42° C. for 18 hours to give 1-cyclohexyl-2-nitroethanol represented by the formula ##STR8## With an optical purity of 90% ee. in a yield of 91%.

Provenance & Evidence