Chem. J. Chinese Universities ›› 2002, Vol. 23 ›› Issue (7): 1318.
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XU Qian-Yong, WU Tong-Xing, PAN Xin-Fu
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Abstract: Four new chiral aminodiols 1-4, which were prepared from methyl L-proline in 2 steps, were applied in the enantioselective addition of diethylzinc to benzaldehyde. The results indicated that the enantioselectivities enhance with increasing the bulkiness of substituents on chiral ligands and with chiral ligand 4 giving the best result. When ligand 4 was used to catalyze the enantioselective addition of diethylzinc to aromatic aldehydes, the substituents affect the enantioselectivities slightly and 1-naphthaldehyde gives the best enantiomeric excess(up to 75.3% ). On the other hand, 4-(dimethylamino)benzaldehyde gives a low enantiomeric excess, which may most likely arise from a non steroselective ethyl transfer to aldehyde promoted by zinc coordination of amino group. For aliphatic aldehydes, poor enantiomeric excesses are generally given.
Key words: Enantioselective addition, Diethylzinc, Chiral aminodiol
CLC Number:
O625
TrendMD:
XU Qian-Yong, WU Tong-Xing, PAN Xin-Fu . Preparation of Chiral Aminodiols and Their Applications in the Catalytic Enantioselective Addition of Diethylzinc to Aldehydes[J]. Chem. J. Chinese Universities, 2002, 23(7): 1318.
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