手性氨基酸酰胺催化二乙基锌与芳香醛不对称加成反应

Enantioselective Addition of Diethylzinc to Aromatic Aldehydes Catalyzed by Modular Amino Acids and Phenylethanamine Based Chiral Ligands

将由磺酰化氨基酸和长链的含甲氧基官能团的胺制备的(S)-N-(4-甲氧基苯乙基)-3-苯基-2-(对甲基苯磺酰胺)丙酰胺(1d)手性配体用于催化二乙基锌与系列芳香醛对映选择性加成反应.15 mol%该催化剂能够对含有吸电子基团、供电子基团及不同位阻的芳香醛均有较好的效果,能够在比较温和的条件下获得高达87%ee和中等程度的产率.

Enantioselective addition of diethylzinc to a series of aromatic aldehydes was developed by chiral ligand（S）-N-（4-methoxyphenethyl）-3-phenyl-2-（tosylamino）propanamide（1d）,which was derivatived from a modular amino acids and long chain amine containg OMe.The catalytic system employing 15 mol% of 1d without using titanium complex was found to promote the addition of diethylzinc（ZnEt2） to a wide range of aromatic aldehydes with electron-donating and elec-tron-withdrawing substituents,giving up to 87% ee of the corresponding secondary alcohol under mild conditions.