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题名: Chiral Ligands derived from Abrine 8. An experimental and theoretical study of free ligand conformational preferences and the addition of diethylzinc to benzaldehyde
作者: Zhu, HJ; Jiang, JX; Saebo, S; Pittman, CU
刊名: JOURNAL OF ORGANIC CHEMISTRY
关键词: CATALYTIC ENANTIOSELECTIVE ADDITION ; BETA-AMINO ALCOHOLS ; DIALKYLZINC REAGENTS ; ASYMMETRIC AUTOCATALYSIS ; ORGANOMETALLIC REAGENTS ; AROMATIC-ALDEHYDES ; AZIRIDINO ALCOHOLS ; CARBONYL-COMPOUNDS ; KETONES ; AMPLIFICATION
英文摘要: 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.
出版日期: 2005-01-07
卷号: 70, 期号:1, 页码:261-267
DOI标识: 10.1021/jo049754c
语种: 英语
ISSN号: 0022-3263
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.kib.ac.cn/handle/151853/4236
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.Kunming Inst Bot, Kunming 650204, Yunnan, Peoples R China
2.Mississippi State Univ, Dept Chem, Mississippi State, MS 39762 USA

Recommended Citation:
Zhu, HJ; Jiang, JX; Saebo, S; Pittman, CU.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,2005,70(1):261-267
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