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题名: 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
作者: Zhu, HJ; Zhao, BT; Zuo, GY; Pittman, CU; Dai, WM; null(郝小江)
刊名: TETRAHEDRON-ASYMMETRY
关键词: CATALYTIC ASYMMETRIC INDUCTION ; AMINO-ALCOHOLS ; ORGANOZINC REAGENTS ; METHYL-ESTER ; DIALKYLZINCS ; BENZALDEHYDE ; DERIVATIVES ; PROMOTERS ; KETONES ; OXAZOLIDINES
英文摘要: 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.
出版日期: 2001-10-15
卷号: 12, 期号:18, 页码:2613-2619
语种: 英语
收录类别: SCI ; IC ; CCR
学科分类: Chemistry, Inorganic & Nuclear; Chemistry, Organic; Chemistry, Physical
ISSN号: 0957-4166
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.kib.ac.cn/handle/151853/4346
Appears in Collections:植物化学与西部植物资源持续利用国家重点实验室_期刊论文

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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

Recommended Citation:
Zhu, HJ; Zhao, BT; Zuo, GY; Pittman, CU; Dai, WM; Hao, XJ.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,2001,12(18):2613-2619
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