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Direct asymmetric aldol reaction of aryl ketones with aryl aldehydes catalyzed by chiral BINOL-derived zincate catalyst.
J Org Chem. 2008 Sep 19; 73(18):7398-401.JO

Abstract

Direct asymmetric aldol reaction of aryl ketones with aryl aldehydes catalyzed by chiral metal complex is reported for the first time herein. Two novel semicrown chiral ligands 1a and 1b were synthesized from (S)- and (R)-BINOL, respectively, and then employed to catalyze the direct asymmetric aldol addition of aryl ketones to aryl aldehydes. Introduced with 2.0 equiv of diethylzinc, 1b had higher enantioselectivity than 1a. Up to 97% yield and up to 80% enantioselectivity were achieved.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Li H
Institute of Biochemistry & Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou 730000, China.
Da CS
No affiliation info available
Xiao YH
No affiliation info available
Li X
No affiliation info available
Su YN
No affiliation info available

MeSH

AldehydesCatalysisKetonesMolecular StructureNaphtholsOrganometallic CompoundsStereoisomerismZinc

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

18700798

Citation

Li, Hong, et al. "Direct Asymmetric Aldol Reaction of Aryl Ketones With Aryl Aldehydes Catalyzed By Chiral BINOL-derived Zincate Catalyst." The Journal of Organic Chemistry, vol. 73, no. 18, 2008, pp. 7398-401.
Li H, Da CS, Xiao YH, et al. Direct asymmetric aldol reaction of aryl ketones with aryl aldehydes catalyzed by chiral BINOL-derived zincate catalyst. J Org Chem. 2008;73(18):7398-401.
Li, H., Da, C. S., Xiao, Y. H., Li, X., & Su, Y. N. (2008). Direct asymmetric aldol reaction of aryl ketones with aryl aldehydes catalyzed by chiral BINOL-derived zincate catalyst. The Journal of Organic Chemistry, 73(18), 7398-401. https://doi.org/10.1021/jo801182n
Li H, et al. Direct Asymmetric Aldol Reaction of Aryl Ketones With Aryl Aldehydes Catalyzed By Chiral BINOL-derived Zincate Catalyst. J Org Chem. 2008 Sep 19;73(18):7398-401. PubMed PMID: 18700798.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Direct asymmetric aldol reaction of aryl ketones with aryl aldehydes catalyzed by chiral BINOL-derived zincate catalyst. AU - Li,Hong, AU - Da,Chao-Shan, AU - Xiao,Yu-Hua, AU - Li,Xiao, AU - Su,Ya-Ning, Y1 - 2008/08/14/ PY - 2008/8/15/pubmed PY - 2008/11/15/medline PY - 2008/8/15/entrez SP - 7398 EP - 401 JF - The Journal of organic chemistry JO - J Org Chem VL - 73 IS - 18 N2 - Direct asymmetric aldol reaction of aryl ketones with aryl aldehydes catalyzed by chiral metal complex is reported for the first time herein. Two novel semicrown chiral ligands 1a and 1b were synthesized from (S)- and (R)-BINOL, respectively, and then employed to catalyze the direct asymmetric aldol addition of aryl ketones to aryl aldehydes. Introduced with 2.0 equiv of diethylzinc, 1b had higher enantioselectivity than 1a. Up to 97% yield and up to 80% enantioselectivity were achieved. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/18700798/Direct_asymmetric_aldol_reaction_of_aryl_ketones_with_aryl_aldehydes_catalyzed_by_chiral_BINOL_derived_zincate_catalyst_ L2 - https://doi.org/10.1021/jo801182n DB - PRIME DP - Unbound Medicine ER -