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Palladium-catalyzed glycal imidate rearrangement: formation of alpha- and beta-N-glycosyl trichloroacetamides.
Org Lett. 2007 Oct 11; 9(21):4231-4.OL

Abstract

A novel palladium(II)-catalyzed stereoselective synthesis of alpha- and beta-N-glycosyl trichloroacetamides has been developed. The alpha- and beta-selectivity at the anomeric carbon depends on the nature of the palladium-ligand catalyst. While the cationic palladium(II) promotes the alpha-selectivity, the neutral palladium(II) favors the beta-selectivity.

Authors+Show Affiliations

Department of Chemistry and Biochemistry, Montana State University, Bozeman, Montana 59717, 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.

Language

eng

PubMed ID

17880097

Citation

Yang, Jaemoon, et al. "Palladium-catalyzed Glycal Imidate Rearrangement: Formation of Alpha- and beta-N-glycosyl Trichloroacetamides." Organic Letters, vol. 9, no. 21, 2007, pp. 4231-4.
Yang J, Mercer GJ, Nguyen HM. Palladium-catalyzed glycal imidate rearrangement: formation of alpha- and beta-N-glycosyl trichloroacetamides. Org Lett. 2007;9(21):4231-4.
Yang, J., Mercer, G. J., & Nguyen, H. M. (2007). Palladium-catalyzed glycal imidate rearrangement: formation of alpha- and beta-N-glycosyl trichloroacetamides. Organic Letters, 9(21), 4231-4.
Yang J, Mercer GJ, Nguyen HM. Palladium-catalyzed Glycal Imidate Rearrangement: Formation of Alpha- and beta-N-glycosyl Trichloroacetamides. Org Lett. 2007 Oct 11;9(21):4231-4. PubMed PMID: 17880097.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-catalyzed glycal imidate rearrangement: formation of alpha- and beta-N-glycosyl trichloroacetamides. AU - Yang,Jaemoon, AU - Mercer,Gregory J, AU - Nguyen,Hien M, Y1 - 2007/09/19/ PY - 2007/9/21/pubmed PY - 2007/12/6/medline PY - 2007/9/21/entrez SP - 4231 EP - 4 JF - Organic letters JO - Org. Lett. VL - 9 IS - 21 N2 - A novel palladium(II)-catalyzed stereoselective synthesis of alpha- and beta-N-glycosyl trichloroacetamides has been developed. The alpha- and beta-selectivity at the anomeric carbon depends on the nature of the palladium-ligand catalyst. While the cationic palladium(II) promotes the alpha-selectivity, the neutral palladium(II) favors the beta-selectivity. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/17880097/Palladium_catalyzed_glycal_imidate_rearrangement:_formation_of_alpha__and_beta_N_glycosyl_trichloroacetamides_ L2 - https://dx.doi.org/10.1021/ol701778z DB - PRIME DP - Unbound Medicine ER -