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A convenient synthesis and the asymmetric hydrogenation of N-phthaloyl dehydroamino acid esters.
Org Lett. 2008 Jul 17; 10(14):3033-6.OL

Abstract

A convenient synthetic method was reported for the preparation of N-phthaloyl dehydroamino acid esters from easily accessible vinyl bromides (or vinyl tosylate) and potassium phthalimide. Rh-catalyzed asymmetric hydrogenation of these substrates with TangPhos gave the products with good to excellent enantioselectivities (up to 99% ee).

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Chen J
College of Chemistry and Molecular Sciences, Wuhan University, P.R. China.
Liu Q
No affiliation info available
Zhang W
No affiliation info available
Spinella S
No affiliation info available
Lei A
No affiliation info available
Zhang X
No affiliation info available

MeSH

Amino AcidsCatalysisCombinatorial Chemistry TechniquesEstersHydrogenationMolecular StructurePhthalic AcidsRhodiumStereoisomerismVinyl Compounds

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

18549236

Citation

Chen, Jian, et al. "A Convenient Synthesis and the Asymmetric Hydrogenation of N-phthaloyl Dehydroamino Acid Esters." Organic Letters, vol. 10, no. 14, 2008, pp. 3033-6.
Chen J, Liu Q, Zhang W, et al. A convenient synthesis and the asymmetric hydrogenation of N-phthaloyl dehydroamino acid esters. Org Lett. 2008;10(14):3033-6.
Chen, J., Liu, Q., Zhang, W., Spinella, S., Lei, A., & Zhang, X. (2008). A convenient synthesis and the asymmetric hydrogenation of N-phthaloyl dehydroamino acid esters. Organic Letters, 10(14), 3033-6. https://doi.org/10.1021/ol800996j
Chen J, et al. A Convenient Synthesis and the Asymmetric Hydrogenation of N-phthaloyl Dehydroamino Acid Esters. Org Lett. 2008 Jul 17;10(14):3033-6. PubMed PMID: 18549236.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A convenient synthesis and the asymmetric hydrogenation of N-phthaloyl dehydroamino acid esters. AU - Chen,Jian, AU - Liu,Qiang, AU - Zhang,Weicheng, AU - Spinella,Stephen, AU - Lei,Aiwen, AU - Zhang,Xumu, Y1 - 2008/06/13/ PY - 2008/6/14/pubmed PY - 2008/9/18/medline PY - 2008/6/14/entrez SP - 3033 EP - 6 JF - Organic letters JO - Org Lett VL - 10 IS - 14 N2 - A convenient synthetic method was reported for the preparation of N-phthaloyl dehydroamino acid esters from easily accessible vinyl bromides (or vinyl tosylate) and potassium phthalimide. Rh-catalyzed asymmetric hydrogenation of these substrates with TangPhos gave the products with good to excellent enantioselectivities (up to 99% ee). SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/18549236/A_convenient_synthesis_and_the_asymmetric_hydrogenation_of_N_phthaloyl_dehydroamino_acid_esters_ L2 - https://doi.org/10.1021/ol800996j DB - PRIME DP - Unbound Medicine ER -