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Enantioselective synthesis of beta2-amino acids using rhodium-catalyzed hydrogenation.
Org Biomol Chem. 2007 Jan 21; 5(2):267-75.OB

Abstract

A series of protected beta2-dehydroamino acids has been prepared in three steps from commercially available starting materials in good yields. These were used as substrates in rhodium-catalyzed asymmetric hydrogenation applying a mixed ligand system of monodentate phosphoramidites and phosphines. Optimization of the catalyst structure was achieved by high throughput experimentation. High enantioselectivities were obtained (up to 91%) with full conversion for a number of beta-amino acids.

Authors+Show Affiliations

Hoen R
Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
Tiemersma-Wegman T
No affiliation info available
Procuranti B
No affiliation info available
Lefort L
No affiliation info available
de Vries JG
No affiliation info available
Minnaard AJ
No affiliation info available
Feringa BL
No affiliation info available

MeSH

AlcoholsAmino AcidsCatalysisChemistry, OrganicHydrogenLigandsMagnetic Resonance SpectroscopyModels, ChemicalPeptidesRhodiumStereoisomerismTemperature

Pub Type(s)

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

Language

eng

PubMed ID

17205170

Citation

Hoen, Rob, et al. "Enantioselective Synthesis of Beta2-amino Acids Using Rhodium-catalyzed Hydrogenation." Organic & Biomolecular Chemistry, vol. 5, no. 2, 2007, pp. 267-75.
Hoen R, Tiemersma-Wegman T, Procuranti B, et al. Enantioselective synthesis of beta2-amino acids using rhodium-catalyzed hydrogenation. Org Biomol Chem. 2007;5(2):267-75.
Hoen, R., Tiemersma-Wegman, T., Procuranti, B., Lefort, L., de Vries, J. G., Minnaard, A. J., & Feringa, B. L. (2007). Enantioselective synthesis of beta2-amino acids using rhodium-catalyzed hydrogenation. Organic & Biomolecular Chemistry, 5(2), 267-75.
Hoen R, et al. Enantioselective Synthesis of Beta2-amino Acids Using Rhodium-catalyzed Hydrogenation. Org Biomol Chem. 2007 Jan 21;5(2):267-75. PubMed PMID: 17205170.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective synthesis of beta2-amino acids using rhodium-catalyzed hydrogenation. AU - Hoen,Rob, AU - Tiemersma-Wegman,Theodora, AU - Procuranti,Barbara, AU - Lefort,Laurent, AU - de Vries,Johannes G, AU - Minnaard,Adriaan J, AU - Feringa,Ben L, Y1 - 2006/12/08/ PY - 2007/1/6/pubmed PY - 2007/4/11/medline PY - 2007/1/6/entrez SP - 267 EP - 75 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 5 IS - 2 N2 - A series of protected beta2-dehydroamino acids has been prepared in three steps from commercially available starting materials in good yields. These were used as substrates in rhodium-catalyzed asymmetric hydrogenation applying a mixed ligand system of monodentate phosphoramidites and phosphines. Optimization of the catalyst structure was achieved by high throughput experimentation. High enantioselectivities were obtained (up to 91%) with full conversion for a number of beta-amino acids. SN - 1477-0520 UR - https://www.unboundmedicine.com/medline/citation/17205170/Enantioselective_synthesis_of_beta2_amino_acids_using_rhodium_catalyzed_hydrogenation_ L2 - https://doi.org/10.1039/b615131k DB - PRIME DP - Unbound Medicine ER -