Chiral Ligands derived from Abrine 8. An experimental and theoretical study of free ligand conformational preferences and the addition of diethylzinc to benzaldehyde
Zhu, HJ; Jiang, JX; Saebo, S; Pittman, CU
2005-01-07
发表期刊JOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
卷号70期号:1页码:261-267
摘要Three structurally similar series of 1,2,3,4-tetrahydro-beta-carboline ligands, 4a-d, 6a-d and 7ad-d, and two series of chiral oxazolidines, 8a-d and 9a-g, were synthesized and used as chiral catalysts in the addition of diethylzinc to benzaldehyde. The enantio selectivities of the resulting 1-phenyl-1-propanol were obtained in each case, and these ee values were, in most cases, related to the conformational populations of the free ligand as expressed by the calculated differences in the energies of the ligand conformations formed by inversion at nitrogen. This suggested the possible existence of a linear free energy relationship. The effect on enantioselectivity of the carbon chain length of the R group located (1) on the C-3 substituent of 4a-d, 6a-d, and 7a-d or (2) at C-5 in 8a-d and 9a-g was studied in detail. On the basis of the correlations observed and the ligands' structural characterization, a structure was proposed for the transition state during ethyl group transfer when using ligands 8a-d. Furthermore, the change in enantioselectivity was successfully predicted when diastereomeric ligands 11 and 12 were compared in this chiral addition.
关键词Catalytic Enantioselective Addition Beta-amino Alcohols Dialkylzinc Reagents Asymmetric Autocatalysis Organometallic Reagents Aromatic-aldehydes Aziridino Alcohols Carbonyl-compounds Ketones Amplification
学科领域Chemistry, Organic
DOI10.1021/jo049754c
收录类别SCI ; IC ; CCR
语种英语
WOS研究方向Chemistry
WOS类目Chemistry, Organic
WOS记录号WOS:000226508600032
引用统计
被引频次:34[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/4236
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.Kunming Inst Bot, Kunming 650204, Yunnan, Peoples R China
2.Mississippi State Univ, Dept Chem, Mississippi State, MS 39762 USA
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Zhu, HJ,Jiang, JX,Saebo, S,et al. Chiral Ligands derived from Abrine 8. An experimental and theoretical study of free ligand conformational preferences and the addition of diethylzinc to benzaldehyde[J]. JOURNAL OF ORGANIC CHEMISTRY,2005,70(1):261-267.
APA Zhu, HJ,Jiang, JX,Saebo, S,&Pittman, CU.(2005).Chiral Ligands derived from Abrine 8. An experimental and theoretical study of free ligand conformational preferences and the addition of diethylzinc to benzaldehyde.JOURNAL OF ORGANIC CHEMISTRY,70(1),261-267.
MLA Zhu, HJ,et al."Chiral Ligands derived from Abrine 8. An experimental and theoretical study of free ligand conformational preferences and the addition of diethylzinc to benzaldehyde".JOURNAL OF ORGANIC CHEMISTRY 70.1(2005):261-267.
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