Abstract
Primary, secondary and tertiary aminodiols were synthetized regio- and stereoselectively from (−)-α-pinene 1 via α-pinene oxide 2, (−)- trans-pinocarveol 3 and key intermediate epoxy alcohol 4. N-Benzyl derivative 5 was transformed to spiro-fused oxazolidine 13 in a highly regioselective ring closure. Aminodiols and their derivatives 5– 13 were applied as chiral catalysts in the enantioselective addition of diethylzinc to benzaldehyde, resulting in chiral 1-phenyl-1-propanol. The substituent effect on the nitrogen was studied in detail and the best enantioselectivity was observed in the case of N-methyl- N-benzyl-substituted derivative 8. The phenomenon was interpreted by using molecular modelling at an ab initio level.
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