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Synthesis of monodentate chiral spiro phosphonites and the electronic effect of ligand in asymmetric hydrogenation.
J Org Chem. 2004 Nov 12; 69(23):8157-60.JO

Abstract

New monodentate chiral phosphonites were synthesized from enantiomerically pure 1,1'-spirobiindane-7,7'-diol. The phosphonites 2 were efficient ligands for the Rh-catalyzed asymmetric hydrogenation of alpha- and beta-dehydroamino acid derivatives, providing the amino acids in high enantioselectivities. The study of electronic effect showed that the electron-withdrawing substitutent on the P-phenyl ring of the phosphonite ligand dramatically decreased both the reactivity and enantioselectivity of the ligand.

Authors+Show Affiliations

State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

15527313

Citation

Fu, Yu, et al. "Synthesis of Monodentate Chiral Spiro Phosphonites and the Electronic Effect of Ligand in Asymmetric Hydrogenation." The Journal of Organic Chemistry, vol. 69, no. 23, 2004, pp. 8157-60.
Fu Y, Hou GH, Xie JH, et al. Synthesis of monodentate chiral spiro phosphonites and the electronic effect of ligand in asymmetric hydrogenation. J Org Chem. 2004;69(23):8157-60.
Fu, Y., Hou, G. H., Xie, J. H., Xing, L., Wang, L. X., & Zhou, Q. L. (2004). Synthesis of monodentate chiral spiro phosphonites and the electronic effect of ligand in asymmetric hydrogenation. The Journal of Organic Chemistry, 69(23), 8157-60.
Fu Y, et al. Synthesis of Monodentate Chiral Spiro Phosphonites and the Electronic Effect of Ligand in Asymmetric Hydrogenation. J Org Chem. 2004 Nov 12;69(23):8157-60. PubMed PMID: 15527313.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of monodentate chiral spiro phosphonites and the electronic effect of ligand in asymmetric hydrogenation. AU - Fu,Yu, AU - Hou,Guo-Hua, AU - Xie,Jian-Hua, AU - Xing,Liang, AU - Wang,Li-Xin, AU - Zhou,Qi-Lin, PY - 2004/11/6/pubmed PY - 2004/11/6/medline PY - 2004/11/6/entrez SP - 8157 EP - 60 JF - The Journal of organic chemistry JO - J Org Chem VL - 69 IS - 23 N2 - New monodentate chiral phosphonites were synthesized from enantiomerically pure 1,1'-spirobiindane-7,7'-diol. The phosphonites 2 were efficient ligands for the Rh-catalyzed asymmetric hydrogenation of alpha- and beta-dehydroamino acid derivatives, providing the amino acids in high enantioselectivities. The study of electronic effect showed that the electron-withdrawing substitutent on the P-phenyl ring of the phosphonite ligand dramatically decreased both the reactivity and enantioselectivity of the ligand. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/15527313/Synthesis_of_monodentate_chiral_spiro_phosphonites_and_the_electronic_effect_of_ligand_in_asymmetric_hydrogenation_ L2 - https://doi.org/10.1021/jo049146x DB - PRIME DP - Unbound Medicine ER -
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