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Enantioselective Rh-catalyzed hydrogenation of N-formyl dehydroamino esters with monodentate phosphoramidite ligands.
J Org Chem. 2006 Mar 03; 71(5):2026-36.JO

Abstract

Enantioselectivities up to >99% ee were achieved in the rhodium-catalyzed asymmetric hydrogenation of N-formyl dehydroamino esters using monodentate phosphoramidites as chiral ligands. The substrates were synthesized by condensation of methyl isocyanoacetate with a range of aldehydes and with cyclohexanone. A highly convenient multigram scale one step synthesis of methyl 2-(formamido)acrylate was developed. This compound was used in the synthesis of methyl 2-(formamido)cinnamate via a solvent free Heck reaction. Moreover, full conversion and >99% ee were obtained in 1 h in the hydrogenation of methyl 2-(formamido)acrylate with 0.2 mol % catalyst and 2 bar hydrogen pressure. The versatility of the formyl protection was established by its removal under mild conditions.

Authors+Show Affiliations

Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.No affiliation info availableNo 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

16496990

Citation

Panella, Lavinia, et al. "Enantioselective Rh-catalyzed Hydrogenation of N-formyl Dehydroamino Esters With Monodentate Phosphoramidite Ligands." The Journal of Organic Chemistry, vol. 71, no. 5, 2006, pp. 2026-36.
Panella L, Aleixandre AM, Kruidhof GJ, et al. Enantioselective Rh-catalyzed hydrogenation of N-formyl dehydroamino esters with monodentate phosphoramidite ligands. J Org Chem. 2006;71(5):2026-36.
Panella, L., Aleixandre, A. M., Kruidhof, G. J., Robertus, J., Feringa, B. L., de Vries, J. G., & Minnaard, A. J. (2006). Enantioselective Rh-catalyzed hydrogenation of N-formyl dehydroamino esters with monodentate phosphoramidite ligands. The Journal of Organic Chemistry, 71(5), 2026-36.
Panella L, et al. Enantioselective Rh-catalyzed Hydrogenation of N-formyl Dehydroamino Esters With Monodentate Phosphoramidite Ligands. J Org Chem. 2006 Mar 3;71(5):2026-36. PubMed PMID: 16496990.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective Rh-catalyzed hydrogenation of N-formyl dehydroamino esters with monodentate phosphoramidite ligands. AU - Panella,Lavinia, AU - Aleixandre,Alicia Marco, AU - Kruidhof,Gerlof J, AU - Robertus,Jort, AU - Feringa,Ben L, AU - de Vries,Johannes G, AU - Minnaard,Adriaan J, PY - 2006/2/25/pubmed PY - 2007/1/16/medline PY - 2006/2/25/entrez SP - 2026 EP - 36 JF - The Journal of organic chemistry JO - J Org Chem VL - 71 IS - 5 N2 - Enantioselectivities up to >99% ee were achieved in the rhodium-catalyzed asymmetric hydrogenation of N-formyl dehydroamino esters using monodentate phosphoramidites as chiral ligands. The substrates were synthesized by condensation of methyl isocyanoacetate with a range of aldehydes and with cyclohexanone. A highly convenient multigram scale one step synthesis of methyl 2-(formamido)acrylate was developed. This compound was used in the synthesis of methyl 2-(formamido)cinnamate via a solvent free Heck reaction. Moreover, full conversion and >99% ee were obtained in 1 h in the hydrogenation of methyl 2-(formamido)acrylate with 0.2 mol % catalyst and 2 bar hydrogen pressure. The versatility of the formyl protection was established by its removal under mild conditions. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/16496990/Enantioselective_Rh_catalyzed_hydrogenation_of_N_formyl_dehydroamino_esters_with_monodentate_phosphoramidite_ligands_ L2 - https://doi.org/10.1021/jo052451d DB - PRIME DP - Unbound Medicine ER -