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First catalytic reductive coupling of 1,3-diynes to carbonyl partners: a new regio- and enantioselective C-C bond forming hydrogenation.
J Am Chem Soc. 2003 Sep 24; 125(38):11488-9.JA

Abstract

Upon exposure of diynes and glyoxals to cationic Rh(I) catalysts under 1 atm of hydrogen gas, regioselective condensation occurs to afford highly unsaturated enyne products without over-reduction. In the presence of chiral phosphine ligands, reductive coupling products are obtained in high enantiomeric excess at ambient temperature and pressure. The present studies are among the first examples of the electrophilic trapping of organometallic intermediates obtained transiently under the conditions of catalytic hydrogenation.

Authors+Show Affiliations

Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, USA.No affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

13129338

Citation

Huddleston, Ryan R., et al. "First Catalytic Reductive Coupling of 1,3-diynes to Carbonyl Partners: a New Regio- and Enantioselective C-C Bond Forming Hydrogenation." Journal of the American Chemical Society, vol. 125, no. 38, 2003, pp. 11488-9.
Huddleston RR, Jang HY, Krische MJ. First catalytic reductive coupling of 1,3-diynes to carbonyl partners: a new regio- and enantioselective C-C bond forming hydrogenation. J Am Chem Soc. 2003;125(38):11488-9.
Huddleston, R. R., Jang, H. Y., & Krische, M. J. (2003). First catalytic reductive coupling of 1,3-diynes to carbonyl partners: a new regio- and enantioselective C-C bond forming hydrogenation. Journal of the American Chemical Society, 125(38), 11488-9.
Huddleston RR, Jang HY, Krische MJ. First Catalytic Reductive Coupling of 1,3-diynes to Carbonyl Partners: a New Regio- and Enantioselective C-C Bond Forming Hydrogenation. J Am Chem Soc. 2003 Sep 24;125(38):11488-9. PubMed PMID: 13129338.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - First catalytic reductive coupling of 1,3-diynes to carbonyl partners: a new regio- and enantioselective C-C bond forming hydrogenation. AU - Huddleston,Ryan R, AU - Jang,Hye-Young, AU - Krische,Michael J, PY - 2003/9/18/pubmed PY - 2003/12/3/medline PY - 2003/9/18/entrez SP - 11488 EP - 9 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 125 IS - 38 N2 - Upon exposure of diynes and glyoxals to cationic Rh(I) catalysts under 1 atm of hydrogen gas, regioselective condensation occurs to afford highly unsaturated enyne products without over-reduction. In the presence of chiral phosphine ligands, reductive coupling products are obtained in high enantiomeric excess at ambient temperature and pressure. The present studies are among the first examples of the electrophilic trapping of organometallic intermediates obtained transiently under the conditions of catalytic hydrogenation. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/13129338/First_catalytic_reductive_coupling_of_13_diynes_to_carbonyl_partners:_a_new_regio__and_enantioselective_C_C_bond_forming_hydrogenation_ L2 - https://doi.org/10.1021/ja030415v DB - PRIME DP - Unbound Medicine ER -