Chiral ligands derived from abrine.: Part 7:: Effect of O, S, N in aromatic ring substituents at C-1 on enantioselectivity induced by tetrahydro-β-carboline ligands in diethylzinc addition to aldehydes

被引:23
作者
Zhu, HJ [1 ]
Zhao, BT
Zuo, GY
Pittman, CU
Dai, WM
Hao, XJ
机构
[1] Mississippi State Univ, Dept Chem, Mississippi State, MS 39762 USA
[2] Chinese Acad Sci, Kunming Inst Bot, Kunming 650204, Yunnan, Peoples R China
[3] HKUST, Dept Chem, Kowloon, Hong Kong, Peoples R China
关键词
D O I
10.1016/S0957-4166(01)00460-8
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The effect or O, S and N atoms in aromatic ring substituents at C-1 position of tetrahydro-B-carboline ligands on the enantioselectivity of diethylzinc additions to benzaldehyde was studied when esters or tertiary alcohol functions were present at C-3. A mechanism is proposed to explain why the ester ligands 2c and 2d, in which the pyridyl N atom is at C'-2 in 2c and at C'-3 in 2d, catalyzed the addition of diethylzinc to benzaldehyde to form the (R)- and (S)-enantiomers of 1-phenyl-1-propanol, respectively. An explanation was also proposed for the moderate enantioselectivity induced by tert-alcohol 3c versus the very small enantioselectivity induced by 3d. containing a 3-pyridyl function at C-1, during diethylzine additions. A -CH2-t-Bu substituent at C-1 leads to very high enantio selectivities. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2613 / 2619
页数:7
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