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A novel class of P-O monophosphite ligands derived from D-mannitol: broad applications in highly enantioselective Rh-catalyzed hydrogenations.
J Org Chem. 2004 Apr 02; 69(7):2355-61.JO

Abstract

We report on a new class of P-O monophosphite ligands (designated 3a-k) with a double six-membered-ring backbone onto which are attached additional groups and on applications of their Rh complexes in the hydrogenation of enamides, alpha-dehydroamino acid esters, dimethyl itaconate, and beta-(acylamino)acrylates. Our results demonstrate that the Rh complexes with ligands 3a-k exhibit high enantioselectivity and reactivity in asymmetric hydrogenation reactions. An ee value of up to 98.0% was obtained for the hydrogenation of alpha-dehydroamino acid esters, and the ee values were all over 99% for the other three types of substrate, with a turnover number of up to 5000.

Authors+Show Affiliations

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

15049630

Citation

Huang, Hanmin, et al. "A Novel Class of P-O Monophosphite Ligands Derived From D-mannitol: Broad Applications in Highly Enantioselective Rh-catalyzed Hydrogenations." The Journal of Organic Chemistry, vol. 69, no. 7, 2004, pp. 2355-61.
Huang H, Zheng Z, Luo H, et al. A novel class of P-O monophosphite ligands derived from D-mannitol: broad applications in highly enantioselective Rh-catalyzed hydrogenations. J Org Chem. 2004;69(7):2355-61.
Huang, H., Zheng, Z., Luo, H., Bai, C., Hu, X., & Chen, H. (2004). A novel class of P-O monophosphite ligands derived from D-mannitol: broad applications in highly enantioselective Rh-catalyzed hydrogenations. The Journal of Organic Chemistry, 69(7), 2355-61.
Huang H, et al. A Novel Class of P-O Monophosphite Ligands Derived From D-mannitol: Broad Applications in Highly Enantioselective Rh-catalyzed Hydrogenations. J Org Chem. 2004 Apr 2;69(7):2355-61. PubMed PMID: 15049630.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A novel class of P-O monophosphite ligands derived from D-mannitol: broad applications in highly enantioselective Rh-catalyzed hydrogenations. AU - Huang,Hanmin, AU - Zheng,Zhuo, AU - Luo,Huili, AU - Bai,Changmin, AU - Hu,Xinquan, AU - Chen,Huilin, PY - 2004/3/31/pubmed PY - 2004/6/4/medline PY - 2004/3/31/entrez SP - 2355 EP - 61 JF - The Journal of organic chemistry JO - J Org Chem VL - 69 IS - 7 N2 - We report on a new class of P-O monophosphite ligands (designated 3a-k) with a double six-membered-ring backbone onto which are attached additional groups and on applications of their Rh complexes in the hydrogenation of enamides, alpha-dehydroamino acid esters, dimethyl itaconate, and beta-(acylamino)acrylates. Our results demonstrate that the Rh complexes with ligands 3a-k exhibit high enantioselectivity and reactivity in asymmetric hydrogenation reactions. An ee value of up to 98.0% was obtained for the hydrogenation of alpha-dehydroamino acid esters, and the ee values were all over 99% for the other three types of substrate, with a turnover number of up to 5000. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/15049630/A_novel_class_of_P_O_monophosphite_ligands_derived_from_D_mannitol:_broad_applications_in_highly_enantioselective_Rh_catalyzed_hydrogenations_ L2 - https://doi.org/10.1021/jo035627p DB - PRIME DP - Unbound Medicine ER -