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Highly efficient asymmetric additions of diethylzinc to aldehydes triply activated by chiral phosphoramide-Zn(II) complexes derived from cinchona alkaloids.
Chirality. 2013 Sep; 25(9):561-6.C

Abstract

New chiral phosphoramide ligands derived from cinchona alkaloids were developed, which react with diethylzinc to form chiral phosphoramide-Zn(II) complexes containing two Lewis bases and one Lewis acid. These trifunctional complexes can serve as highly efficient chiral catalysts for triple activation of enantioselective addition reactions of diethylzinc with aldehydes to give desired alcohol products with excellent yields and enantiomeric excess (ee) values up to 99%.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Shen B
The Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Chinese Academy of Sciences, Fuzhou, Fujian, China.
Huang H
No affiliation info available
Bian G
No affiliation info available
Zong H
No affiliation info available
Song L
No affiliation info available

MeSH

AldehydesCatalysisCinchona AlkaloidsLigandsMolecular StructureOrganometallic CompoundsPhosphoramidesQuinineStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

23798341

Citation

Shen, Bin, et al. "Highly Efficient Asymmetric Additions of Diethylzinc to Aldehydes Triply Activated By Chiral phosphoramide-Zn(II) Complexes Derived From Cinchona Alkaloids." Chirality, vol. 25, no. 9, 2013, pp. 561-6.
Shen B, Huang H, Bian G, et al. Highly efficient asymmetric additions of diethylzinc to aldehydes triply activated by chiral phosphoramide-Zn(II) complexes derived from cinchona alkaloids. Chirality. 2013;25(9):561-6.
Shen, B., Huang, H., Bian, G., Zong, H., & Song, L. (2013). Highly efficient asymmetric additions of diethylzinc to aldehydes triply activated by chiral phosphoramide-Zn(II) complexes derived from cinchona alkaloids. Chirality, 25(9), 561-6. https://doi.org/10.1002/chir.22171
Shen B, et al. Highly Efficient Asymmetric Additions of Diethylzinc to Aldehydes Triply Activated By Chiral phosphoramide-Zn(II) Complexes Derived From Cinchona Alkaloids. Chirality. 2013;25(9):561-6. PubMed PMID: 23798341.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly efficient asymmetric additions of diethylzinc to aldehydes triply activated by chiral phosphoramide-Zn(II) complexes derived from cinchona alkaloids. AU - Shen,Bin, AU - Huang,Huayin, AU - Bian,Guangling, AU - Zong,Hua, AU - Song,Ling, Y1 - 2013/06/25/ PY - 2013/01/18/received PY - 2013/02/27/accepted PY - 2013/6/27/entrez PY - 2013/6/27/pubmed PY - 2014/3/14/medline KW - cinchona alkaloids KW - diethylzinc KW - enantioselective addition KW - phosphoramide KW - triple activation SP - 561 EP - 6 JF - Chirality JO - Chirality VL - 25 IS - 9 N2 - New chiral phosphoramide ligands derived from cinchona alkaloids were developed, which react with diethylzinc to form chiral phosphoramide-Zn(II) complexes containing two Lewis bases and one Lewis acid. These trifunctional complexes can serve as highly efficient chiral catalysts for triple activation of enantioselective addition reactions of diethylzinc with aldehydes to give desired alcohol products with excellent yields and enantiomeric excess (ee) values up to 99%. SN - 1520-636X UR - https://www.unboundmedicine.com/medline/citation/23798341/Highly_efficient_asymmetric_additions_of_diethylzinc_to_aldehydes_triply_activated_by_chiral_phosphoramide_Zn_II__complexes_derived_from_cinchona_alkaloids_ L2 - https://doi.org/10.1002/chir.22171 DB - PRIME DP - Unbound Medicine ER -