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Synthesis of a new chiral bisphospholane ligand for the Rh(I)-catalyzed enantioselective hydrogenation of isomeric beta-acylamido acrylates.
J Org Chem. 2003 Mar 07; 68(5):1701-7.JO

Abstract

The highly stereoselective synthesis of a chiral silylphospholane has been described, which can be advantageously used as a building block under base-free conditions for the construction of diphosphines related to DuPHOS. The utility of silylphospholane is shown in the synthesis of a new bisphospholane ligand 1 (MalPHOS), which is characterized by a maleic anhydride backbone. The ligand forms with Rh(I) a complex with a larger bite angle P-Rh-P than the analogue Me-DuPHOS complex. Both complexes have been tested in the asymmetric hydrogenation of unsaturated alpha- and beta-amino acid precursors of pharmaceutical relevance. In several cases, the new catalyst was superior in comparison to the Me-DuPHOS complex, in particular when (Z)-configured beta-acylamido acrylates were used as substrates.

Authors+Show Affiliations

Holz J
Institut für Organische Katalyseforschung an der Universität Rostock e.V., Buchbinderstr. 5/6, 18055 Rostock, Germany. jens.holz@ifok.uni-rostock.de
Monsees A
No affiliation info available
Jiao H
No affiliation info available
You J
No affiliation info available
Komarov IV
No affiliation info available
Fischer C
No affiliation info available
Drauz K
No affiliation info available
Börner A
No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

12608781

Citation

Holz, Jens, et al. "Synthesis of a New Chiral Bisphospholane Ligand for the Rh(I)-catalyzed Enantioselective Hydrogenation of Isomeric Beta-acylamido Acrylates." The Journal of Organic Chemistry, vol. 68, no. 5, 2003, pp. 1701-7.
Holz J, Monsees A, Jiao H, et al. Synthesis of a new chiral bisphospholane ligand for the Rh(I)-catalyzed enantioselective hydrogenation of isomeric beta-acylamido acrylates. J Org Chem. 2003;68(5):1701-7.
Holz, J., Monsees, A., Jiao, H., You, J., Komarov, I. V., Fischer, C., Drauz, K., & Börner, A. (2003). Synthesis of a new chiral bisphospholane ligand for the Rh(I)-catalyzed enantioselective hydrogenation of isomeric beta-acylamido acrylates. The Journal of Organic Chemistry, 68(5), 1701-7.
Holz J, et al. Synthesis of a New Chiral Bisphospholane Ligand for the Rh(I)-catalyzed Enantioselective Hydrogenation of Isomeric Beta-acylamido Acrylates. J Org Chem. 2003 Mar 7;68(5):1701-7. PubMed PMID: 12608781.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of a new chiral bisphospholane ligand for the Rh(I)-catalyzed enantioselective hydrogenation of isomeric beta-acylamido acrylates. AU - Holz,Jens, AU - Monsees,Axel, AU - Jiao,Haijun, AU - You,Jinsong, AU - Komarov,Igor V, AU - Fischer,Christine, AU - Drauz,Karlheinz, AU - Börner,Armin, PY - 2003/3/1/pubmed PY - 2003/3/1/medline PY - 2003/3/1/entrez SP - 1701 EP - 7 JF - The Journal of organic chemistry JO - J Org Chem VL - 68 IS - 5 N2 - The highly stereoselective synthesis of a chiral silylphospholane has been described, which can be advantageously used as a building block under base-free conditions for the construction of diphosphines related to DuPHOS. The utility of silylphospholane is shown in the synthesis of a new bisphospholane ligand 1 (MalPHOS), which is characterized by a maleic anhydride backbone. The ligand forms with Rh(I) a complex with a larger bite angle P-Rh-P than the analogue Me-DuPHOS complex. Both complexes have been tested in the asymmetric hydrogenation of unsaturated alpha- and beta-amino acid precursors of pharmaceutical relevance. In several cases, the new catalyst was superior in comparison to the Me-DuPHOS complex, in particular when (Z)-configured beta-acylamido acrylates were used as substrates. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/12608781/Synthesis_of_a_new_chiral_bisphospholane_ligand_for_the_Rh_I__catalyzed_enantioselective_hydrogenation_of_isomeric_beta_acylamido_acrylates_ DB - PRIME DP - Unbound Medicine ER -