ICCAS OpenIR
Dendritic BINOL ligands for asymmetric catalysis: effect of the linking positions and generations of the dendritic wedges on catalyst properties
Liu, GH; Tang, WJ; Fan, QH
2003-10-20
Source PublicationTETRAHEDRON
ISSN0040-4020
Volume59Issue:43Pages:8603-8611
AbstractThree types of new chiral BINOL ligands (2, 3 and 4) bearing dendritic wedges have been synthesized through coupling reaction between 3-hydroxymethyl-2,2'-bis(methoxymethyl)-1,1'-binaphthol (7), 6,6'-dihydroxymethyl-2,2'-bis(methoxymethyl)-1,1'-binaphthol (12), 6-hydroxymethyl-2,2'-bis(methoxymethyl)-1,1'-binaphthol (15) and Frechet-type polyether dendritic benzyl bromide, followed by deprotection of methoxymethyl groups by (PrOH)-Pr-i/HCl, respectively. These new ligands obtained were assessed in enantioselective Lewis acid-catalyzed addition of diethylzinc to benzaldehyde. Compared to the enantioselectivity observed with dendrimer 1 bearing the dendritic wedges at 3,3'-positions of the binaphthyl backbone, higher enantioselectivity for all these ligands was observed. Difference in the effect of linking positions and generations on enantioselectivity and/or activity for all three kinds of dendritic ligand-derived catalysts was observed. Among these dendritic ligands, (R)-3/Ti(IV) catalyst with the dendritic wedges at 6,6-positions of BINOL gave the highest enantioselectivity (up to 87% ee). (C) 2003 Elsevier Ltd. All rights reserved.
KeywordChiral Dendrimer Asymmetric Catalysis Alkylation Binol
DOI10.1016/j.tet.2003.09.030
Indexed BySCI ; IC
Language英语
WOS IDWOS:000186109100014
PublisherPERGAMON-ELSEVIER SCIENCE LTD
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Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/79876
Collection中国科学院化学研究所
Corresponding AuthorFan, QH
Affiliation1.Chinese Acad Sci, Inst Chem, Biol Chem Lab, Beijing 100080, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
Recommended Citation
GB/T 7714
Liu, GH,Tang, WJ,Fan, QH. Dendritic BINOL ligands for asymmetric catalysis: effect of the linking positions and generations of the dendritic wedges on catalyst properties[J]. TETRAHEDRON,2003,59(43):8603-8611.
APA Liu, GH,Tang, WJ,&Fan, QH.(2003).Dendritic BINOL ligands for asymmetric catalysis: effect of the linking positions and generations of the dendritic wedges on catalyst properties.TETRAHEDRON,59(43),8603-8611.
MLA Liu, GH,et al."Dendritic BINOL ligands for asymmetric catalysis: effect of the linking positions and generations of the dendritic wedges on catalyst properties".TETRAHEDRON 59.43(2003):8603-8611.
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