Primary, secondary and tertiary γ-amino alcohols 4, 5, 7 and 9 and 1,3-diamine 6 were synthesized from (+)- and (-)-α-pinene 1 via chiral N-Boc β-amino ester 3a and carboxamide 3b. The amino alcohols and diamine obtained were applied as chiral catalysts in the enantioselective addition of diethylzinc to aromatic aldehydes, resulting in chiral 1-aryl-1-propanols. The first evidence of the substituent-dependent enantioselectivity of 1,3-amino alcohol catalysts was observed, and the phenomenon interpreted by using molecular modelling at the ab initio level.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry