| Chiral ligands derived from abrine. Part 7: Effect of O, S, N in aromatic ring substituents at C-1 on enantioselectivity induced by tetrahydro-beta-carboline ligands in diethylzinc addition to aldehydes | |
Zhu, HJ; Zhao, BT; Zuo, GY; Pittman, CU; Dai, WM; Hao, XJ
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| 2001-10-15 | |
| 发表期刊 | TETRAHEDRON-ASYMMETRY
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| ISSN | 0957-4166 |
| 卷号 | 12期号:18页码:2613-2619 |
| 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. |
| 关键词 | Catalytic Asymmetric Induction Amino-alcohols Organozinc Reagents Methyl-ester Dialkylzincs Benzaldehyde Derivatives Promoters Ketones Oxazolidines |
| 学科领域 | Chemistry, Inorganic & Nuclear ; Chemistry, Organic ; Chemistry, Physical |
| 收录类别 | SCI ; IC ; CCR |
| 语种 | 英语 |
| WOS记录号 | WOS:000172642400017 |
| 引用统计 | |
| 文献类型 | 期刊论文 |
| 条目标识符 | http://ir.kib.ac.cn/handle/151853/4346 |
| 专题 | 植物化学与西部植物资源持续利用国家重点实验室 |
| 作者单位 | 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 |
| 推荐引用方式 GB/T 7714 | Zhu, HJ,Zhao, BT,Zuo, GY,et al. Chiral ligands derived from abrine. Part 7: Effect of O, S, N in aromatic ring substituents at C-1 on enantioselectivity induced by tetrahydro-beta-carboline ligands in diethylzinc addition to aldehydes[J]. TETRAHEDRON-ASYMMETRY,2001,12(18):2613-2619. |
| APA | Zhu, HJ,Zhao, BT,Zuo, GY,Pittman, CU,Dai, WM,&Hao, XJ.(2001).Chiral ligands derived from abrine. Part 7: Effect of O, S, N in aromatic ring substituents at C-1 on enantioselectivity induced by tetrahydro-beta-carboline ligands in diethylzinc addition to aldehydes.TETRAHEDRON-ASYMMETRY,12(18),2613-2619. |
| MLA | Zhu, HJ,et al."Chiral ligands derived from abrine. Part 7: Effect of O, S, N in aromatic ring substituents at C-1 on enantioselectivity induced by tetrahydro-beta-carboline ligands in diethylzinc addition to aldehydes".TETRAHEDRON-ASYMMETRY 12.18(2001):2613-2619. |
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