手性氨基二醇的合成及其在二乙基锌对醛不对称加成反应中的应用  

Preparation of Chiral Aminodiols and Their Applications in the Catalytic Enantioselective Addition of Diethylzinc to Aldehydes

作　　者：徐前永[1] 武同兴[1] 潘鑫复[1] 

机构地区：[1]兰州大学化学系

出　　处：《高等学校化学学报》2002年第7期1318-1320,共3页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金 (批准号 :2 0 172 0 2 3 )

摘　　要：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.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.

关 键 词：合成 醛 不对称加成反应 二乙基锌 手性氨基二醇 手性配体 催化剂 

分 类 号：O623.51[理学—有机化学] O621.34[理学—化学]