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Zinc-mediated asymmetric additions of dialkylphosphine oxides to α,β-unsaturated ketones and N-sulfinylimines.
J Org Chem. 2010 Oct 15; 75(20):6756-63.JO

Abstract

A catalyst was synthesized on the basis of Trost's dinuclear catalyst characterized by working well without pyridine in the present phospha-Michael reaction. Nevertheless, the presence of pyridine is still advantageous in the present system. The substrate scope was successfully extended to enones employing diallyl phosphine oxide as a nucleophile. Excellent yields and enantioselectivities (up to >99% ee) were achieved for a wide scope of enones employing the catalyst under mild conditions. The detailed reaction mechanism is also discussed herein. Finally, the unprecedented asymmetric additions of dialkylphosphine oxides to N-sulfinylimines were achieved by using Et(2)Zn as a base.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zhao D
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Medicine, State Key Laboratory of Applied Organic Chemistry, and Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou 730000, PR China.
Mao L
No affiliation info available
Yang D
No affiliation info available
Wang R
No affiliation info available

MeSH

CatalysisIminesKetonesMolecular StructureOrganometallic CompoundsOxidesPhosphinesStereoisomerismZinc

Pub Type(s)

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

Language

eng

PubMed ID

20845966

Citation

Zhao, Depeng, et al. "Zinc-mediated Asymmetric Additions of Dialkylphosphine Oxides to Α,β-unsaturated Ketones and N-sulfinylimines." The Journal of Organic Chemistry, vol. 75, no. 20, 2010, pp. 6756-63.
Zhao D, Mao L, Yang D, et al. Zinc-mediated asymmetric additions of dialkylphosphine oxides to α,β-unsaturated ketones and N-sulfinylimines. J Org Chem. 2010;75(20):6756-63.
Zhao, D., Mao, L., Yang, D., & Wang, R. (2010). Zinc-mediated asymmetric additions of dialkylphosphine oxides to α,β-unsaturated ketones and N-sulfinylimines. The Journal of Organic Chemistry, 75(20), 6756-63. https://doi.org/10.1021/jo1014917
Zhao D, et al. Zinc-mediated Asymmetric Additions of Dialkylphosphine Oxides to Α,β-unsaturated Ketones and N-sulfinylimines. J Org Chem. 2010 Oct 15;75(20):6756-63. PubMed PMID: 20845966.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Zinc-mediated asymmetric additions of dialkylphosphine oxides to α,β-unsaturated ketones and N-sulfinylimines. AU - Zhao,Depeng, AU - Mao,Lijuan, AU - Yang,Dongxu, AU - Wang,Rui, PY - 2010/9/18/entrez PY - 2010/9/18/pubmed PY - 2011/1/28/medline SP - 6756 EP - 63 JF - The Journal of organic chemistry JO - J Org Chem VL - 75 IS - 20 N2 - A catalyst was synthesized on the basis of Trost's dinuclear catalyst characterized by working well without pyridine in the present phospha-Michael reaction. Nevertheless, the presence of pyridine is still advantageous in the present system. The substrate scope was successfully extended to enones employing diallyl phosphine oxide as a nucleophile. Excellent yields and enantioselectivities (up to >99% ee) were achieved for a wide scope of enones employing the catalyst under mild conditions. The detailed reaction mechanism is also discussed herein. Finally, the unprecedented asymmetric additions of dialkylphosphine oxides to N-sulfinylimines were achieved by using Et(2)Zn as a base. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/20845966/Zinc_mediated_asymmetric_additions_of_dialkylphosphine_oxides_to_αβ_unsaturated_ketones_and_N_sulfinylimines_ L2 - https://doi.org/10.1021/jo1014917 DB - PRIME DP - Unbound Medicine ER -