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A highly diastereo- and enantioselective copper(I)-catalyzed Henry reaction using a bis(sulfonamide)-diamine ligand.
J Org Chem. 2011 Jan 21; 76(2):484-91.JO

Abstract

A series of bis(sulfonamide)-diamine (BSDA) ligands were synthesized from commercially available chiral α-amino alcohols and diamines. The chiral BSDA ligand 3a, coordinated with Cu(I), catalyzes the enantioselective Henry reaction with excellent enantioselectivity (up to 99%). Moreover, with the assistance of pyridine, a CuBr-3a system promotes the diastereoselective Henry reaction with various aldehyde substrates and gives the corresponding syn-selective adduct with up to a 99% yield and 32.3:1 syn/anti selectivity. The enantiomeric excess of the syn adduct was 97%.

Authors+Show Affiliations

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

Pub Type(s)

Journal Article

Language

eng

PubMed ID

21174471

Citation

Jin, Wei, et al. "A Highly Diastereo- and Enantioselective copper(I)-catalyzed Henry Reaction Using a Bis(sulfonamide)-diamine Ligand." The Journal of Organic Chemistry, vol. 76, no. 2, 2011, pp. 484-91.
Jin W, Li X, Wan B. A highly diastereo- and enantioselective copper(I)-catalyzed Henry reaction using a bis(sulfonamide)-diamine ligand. J Org Chem. 2011;76(2):484-91.
Jin, W., Li, X., & Wan, B. (2011). A highly diastereo- and enantioselective copper(I)-catalyzed Henry reaction using a bis(sulfonamide)-diamine ligand. The Journal of Organic Chemistry, 76(2), 484-91. https://doi.org/10.1021/jo101932a
Jin W, Li X, Wan B. A Highly Diastereo- and Enantioselective copper(I)-catalyzed Henry Reaction Using a Bis(sulfonamide)-diamine Ligand. J Org Chem. 2011 Jan 21;76(2):484-91. PubMed PMID: 21174471.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A highly diastereo- and enantioselective copper(I)-catalyzed Henry reaction using a bis(sulfonamide)-diamine ligand. AU - Jin,Wei, AU - Li,Xincheng, AU - Wan,Boshun, Y1 - 2010/12/21/ PY - 2010/12/23/entrez PY - 2010/12/23/pubmed PY - 2010/12/23/medline SP - 484 EP - 91 JF - The Journal of organic chemistry JO - J Org Chem VL - 76 IS - 2 N2 - A series of bis(sulfonamide)-diamine (BSDA) ligands were synthesized from commercially available chiral α-amino alcohols and diamines. The chiral BSDA ligand 3a, coordinated with Cu(I), catalyzes the enantioselective Henry reaction with excellent enantioselectivity (up to 99%). Moreover, with the assistance of pyridine, a CuBr-3a system promotes the diastereoselective Henry reaction with various aldehyde substrates and gives the corresponding syn-selective adduct with up to a 99% yield and 32.3:1 syn/anti selectivity. The enantiomeric excess of the syn adduct was 97%. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/21174471/A_highly_diastereo__and_enantioselective_copper_I__catalyzed_Henry_reaction_using_a_bis_sulfonamide__diamine_ligand_ L2 - https://doi.org/10.1021/jo101932a DB - PRIME DP - Unbound Medicine ER -
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