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
2001-10-15
Source PublicationTETRAHEDRON-ASYMMETRY
ISSN0957-4166
Volume12Issue:18Pages:2613-2619
AbstractThe 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.
KeywordCatalytic Asymmetric Induction Amino-alcohols Organozinc Reagents Methyl-ester Dialkylzincs Benzaldehyde Derivatives Promoters Ketones Oxazolidines
Subject AreaChemistry, Inorganic & Nuclear ; Chemistry, Organic ; Chemistry, Physical
Indexed BySCI ; IC ; CCR
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Inorganic & Nuclear ; Chemistry, Organic ; Chemistry, Physical
WOS IDWOS:000172642400017
Citation statistics
Cited Times:22[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/4346
Collection植物化学与西部植物资源持续利用国家重点实验室
Affiliation1.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
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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