Chiral Ligands derived from Abrine 8. An experimental and theoretical study of free ligand conformational preferences and the addition of diethylzinc to benzaldehyde

doi:10.1021/jo049754c

CORC > 昆明植物研究所 > 中国科学院昆明植物研究所 > 植物化学与西部植物资源持续利用国家重点实验室

	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
刊名	JOURNAL OF ORGANIC CHEMISTRY
	2005-01-07
卷号	70 期号:1 页码:261-267
关键词	Catalytic Enantioselective Addition Beta-amino Alcohols Dialkylzinc Reagents Asymmetric Autocatalysis Organometallic Reagents Aromatic-aldehydes Aziridino Alcohols Carbonyl-compounds Ketones Amplification
ISSN号	0022-3263
DOI	10.1021/jo049754c
文献子类	Article
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.
学科主题	Chemistry, Organic
WOS关键词	CATALYTIC ENANTIOSELECTIVE ADDITION ; BETA-AMINO ALCOHOLS ; DIALKYLZINC REAGENTS ; ASYMMETRIC AUTOCATALYSIS ; ORGANOMETALLIC REAGENTS ; AROMATIC-ALDEHYDES ; AZIRIDINO ALCOHOLS ; CARBONYL-COMPOUNDS ; KETONES ; AMPLIFICATION
WOS研究方向	Chemistry
语种	英语
WOS记录号	WOS:000226508600032
公开日期	2012-03-21
内容类型	期刊论文
源URL	[http://ir.kib.ac.cn:8080/handle/151853/4236]
专题	昆明植物研究所_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
推荐引用方式 GB/T 7714	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.