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Enantioselective Rh-catalyzed hydrogenation of 3-aryl-4-phosphonobutenoates with a P-stereogenic BoPhoz-type ligand.
J Org Chem. 2010 Dec 03; 75(23):8319-21.JO

Abstract

A series of chiral 3-aryl-4-phosphonobutyric acid esters were synthesized in high enantioselectivities (93-98% ee) via the Rh-catalyzed asymmetric hydrogenation of the corresponding 3-aryl-4-phosphonobutenoates using a P-stereogenic BoPhoz-type phosphine-aminophosphine ligand. The methodology has been successfully applied to the asymmetric synthesis of a potential GABA(B) antagonist, (R)-phaclofen, in high enantioselectivity.

Authors+Show Affiliations

Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

21062052

Citation

Duan, Zheng-Chao, et al. "Enantioselective Rh-catalyzed Hydrogenation of 3-aryl-4-phosphonobutenoates With a P-stereogenic BoPhoz-type Ligand." The Journal of Organic Chemistry, vol. 75, no. 23, 2010, pp. 8319-21.
Duan ZC, Hu XP, Zhang C, et al. Enantioselective Rh-catalyzed hydrogenation of 3-aryl-4-phosphonobutenoates with a P-stereogenic BoPhoz-type ligand. J Org Chem. 2010;75(23):8319-21.
Duan, Z. C., Hu, X. P., Zhang, C., & Zheng, Z. (2010). Enantioselective Rh-catalyzed hydrogenation of 3-aryl-4-phosphonobutenoates with a P-stereogenic BoPhoz-type ligand. The Journal of Organic Chemistry, 75(23), 8319-21. https://doi.org/10.1021/jo101849b
Duan ZC, et al. Enantioselective Rh-catalyzed Hydrogenation of 3-aryl-4-phosphonobutenoates With a P-stereogenic BoPhoz-type Ligand. J Org Chem. 2010 Dec 3;75(23):8319-21. PubMed PMID: 21062052.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective Rh-catalyzed hydrogenation of 3-aryl-4-phosphonobutenoates with a P-stereogenic BoPhoz-type ligand. AU - Duan,Zheng-Chao, AU - Hu,Xiang-Ping, AU - Zhang,Cheng, AU - Zheng,Zhuo, Y1 - 2010/11/09/ PY - 2010/11/11/entrez PY - 2010/11/11/pubmed PY - 2011/2/16/medline SP - 8319 EP - 21 JF - The Journal of organic chemistry JO - J Org Chem VL - 75 IS - 23 N2 - A series of chiral 3-aryl-4-phosphonobutyric acid esters were synthesized in high enantioselectivities (93-98% ee) via the Rh-catalyzed asymmetric hydrogenation of the corresponding 3-aryl-4-phosphonobutenoates using a P-stereogenic BoPhoz-type phosphine-aminophosphine ligand. The methodology has been successfully applied to the asymmetric synthesis of a potential GABA(B) antagonist, (R)-phaclofen, in high enantioselectivity. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/21062052/Enantioselective_Rh_catalyzed_hydrogenation_of_3_aryl_4_phosphonobutenoates_with_a_P_stereogenic_BoPhoz_type_ligand_ L2 - https://doi.org/10.1021/jo101849b DB - PRIME DP - Unbound Medicine ER -