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Highly stereoselective Michael addition reactions of CamTHP*-desymmetrized glycinamide for the synthesis of functionally dense amino acid derivatives.
Org Lett. 2004 Nov 25; 6(24):4427-9.OL

Abstract

The camphor-derived tetrahydropyran (camTHP*)-desymmetrized glycinamide 1 undergoes efficient and highly diastereoselective lithium enolate Michael additions to nitro olefins, alpha,beta-unsaturated ketones, esters, and lactones. Straightforward manipulation of these products affords 3-substituted pyroglutamides and beta-aryl-alpha,gamma-diamino acid derivatives, highlighting the ease of synthesis of enantiomerically enriched, functionally dense molecules using this novel building block. [reaction: see text]

Authors+Show Affiliations

Dixon DJ
Department of Chemistry, University of Manchester, Manchester, M13 9PL, U.K. darren.dixon@man.ac.uk
Horan RA
No affiliation info available
Monck NJ
No affiliation info available
Berg P
No affiliation info available

MeSH

Amino AcidsCamphorGlycineStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

15548042

Citation

Dixon, Darren J., et al. "Highly Stereoselective Michael Addition Reactions of CamTHP*-desymmetrized Glycinamide for the Synthesis of Functionally Dense Amino Acid Derivatives." Organic Letters, vol. 6, no. 24, 2004, pp. 4427-9.
Dixon DJ, Horan RA, Monck NJ, et al. Highly stereoselective Michael addition reactions of CamTHP*-desymmetrized glycinamide for the synthesis of functionally dense amino acid derivatives. Org Lett. 2004;6(24):4427-9.
Dixon, D. J., Horan, R. A., Monck, N. J., & Berg, P. (2004). Highly stereoselective Michael addition reactions of CamTHP*-desymmetrized glycinamide for the synthesis of functionally dense amino acid derivatives. Organic Letters, 6(24), 4427-9.
Dixon DJ, et al. Highly Stereoselective Michael Addition Reactions of CamTHP*-desymmetrized Glycinamide for the Synthesis of Functionally Dense Amino Acid Derivatives. Org Lett. 2004 Nov 25;6(24):4427-9. PubMed PMID: 15548042.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly stereoselective Michael addition reactions of CamTHP*-desymmetrized glycinamide for the synthesis of functionally dense amino acid derivatives. AU - Dixon,Darren J, AU - Horan,Richard A J, AU - Monck,Nathaniel J T, AU - Berg,Paul, PY - 2004/11/19/pubmed PY - 2006/1/25/medline PY - 2004/11/19/entrez SP - 4427 EP - 9 JF - Organic letters JO - Org Lett VL - 6 IS - 24 N2 - The camphor-derived tetrahydropyran (camTHP*)-desymmetrized glycinamide 1 undergoes efficient and highly diastereoselective lithium enolate Michael additions to nitro olefins, alpha,beta-unsaturated ketones, esters, and lactones. Straightforward manipulation of these products affords 3-substituted pyroglutamides and beta-aryl-alpha,gamma-diamino acid derivatives, highlighting the ease of synthesis of enantiomerically enriched, functionally dense molecules using this novel building block. [reaction: see text] SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/15548042/Highly_stereoselective_Michael_addition_reactions_of_CamTHP__desymmetrized_glycinamide_for_the_synthesis_of_functionally_dense_amino_acid_derivatives_ DB - PRIME DP - Unbound Medicine ER -
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