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Hydrogen bonding makes a difference in the rhodium-catalyzed enantioselective hydrogenation using monodentate phosphoramidites.
J Am Chem Soc. 2006 Nov 08; 128(44):14212-3.JA

Abstract

A new generation of monodentate phosphoramidite ligands bearing a primary amine moiety was found to display comparable or better efficiency than bisphosphines in the Rh-catalyzed asymmetric hydrogenation of challenging substrates, such as (Z)-methyl alpha-acetoxyacrylate or (E)-beta-aryl itaconate derivatives, affording the corresponding hydrogenation products with excellent enantioselectivities (up to >99% ee). The presence of intermolecular hydrogen bonding (HB) between two monodentate ligands in the catalyst was found to be critical for excellent catalyst performance. This finding provides a basis for design and development of further catalyst systems using this type of monodentate phosphoramidite ligands.

Authors+Show Affiliations

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, PR China.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

17076467

Citation

Liu, Yan, et al. "Hydrogen Bonding Makes a Difference in the Rhodium-catalyzed Enantioselective Hydrogenation Using Monodentate Phosphoramidites." Journal of the American Chemical Society, vol. 128, no. 44, 2006, pp. 14212-3.
Liu Y, Sandoval CA, Yamaguchi Y, et al. Hydrogen bonding makes a difference in the rhodium-catalyzed enantioselective hydrogenation using monodentate phosphoramidites. J Am Chem Soc. 2006;128(44):14212-3.
Liu, Y., Sandoval, C. A., Yamaguchi, Y., Zhang, X., Wang, Z., Kato, K., & Ding, K. (2006). Hydrogen bonding makes a difference in the rhodium-catalyzed enantioselective hydrogenation using monodentate phosphoramidites. Journal of the American Chemical Society, 128(44), 14212-3.
Liu Y, et al. Hydrogen Bonding Makes a Difference in the Rhodium-catalyzed Enantioselective Hydrogenation Using Monodentate Phosphoramidites. J Am Chem Soc. 2006 Nov 8;128(44):14212-3. PubMed PMID: 17076467.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Hydrogen bonding makes a difference in the rhodium-catalyzed enantioselective hydrogenation using monodentate phosphoramidites. AU - Liu,Yan, AU - Sandoval,Christian A, AU - Yamaguchi,Yoshiki, AU - Zhang,Xue, AU - Wang,Zheng, AU - Kato,Koichi, AU - Ding,Kuiling, PY - 2006/11/2/pubmed PY - 2007/10/12/medline PY - 2006/11/2/entrez SP - 14212 EP - 3 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 128 IS - 44 N2 - A new generation of monodentate phosphoramidite ligands bearing a primary amine moiety was found to display comparable or better efficiency than bisphosphines in the Rh-catalyzed asymmetric hydrogenation of challenging substrates, such as (Z)-methyl alpha-acetoxyacrylate or (E)-beta-aryl itaconate derivatives, affording the corresponding hydrogenation products with excellent enantioselectivities (up to >99% ee). The presence of intermolecular hydrogen bonding (HB) between two monodentate ligands in the catalyst was found to be critical for excellent catalyst performance. This finding provides a basis for design and development of further catalyst systems using this type of monodentate phosphoramidite ligands. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/17076467/Hydrogen_bonding_makes_a_difference_in_the_rhodium_catalyzed_enantioselective_hydrogenation_using_monodentate_phosphoramidites_ L2 - https://doi.org/10.1021/ja063350f DB - PRIME DP - Unbound Medicine ER -