Enantioselective addition of diethylzinc to aldehydes catalyzed by γ-amino alcohols derived from (+)- and (?)-α-pinene |
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| Institution: | 1. Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, Japan;2. Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan;3. Osaka University of Pharmaceutical Sciences, Osaka 569-1094, Japan;4. Division of Organic Chemistry, National Institute of Health Sciences, Tokyo 158-8501, Japan;1. Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, H-6720 Szeged, Hungary;2. Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös utca 6, H-6720 Szeged, Hungary;3. Department of Analytical Chemistry, University of Vienna, Währinger Strasse 83, 1090 Vienna, Austria |
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| Abstract: | 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. |
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