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Asymmetric synthesis of quaternary alpha- and beta-amino acids and beta-lactams via proline-catalyzed mannich reactions with branched aldehyde donors.
Org Lett. 2004 Jul 22; 6(15):2507-10.OL

Abstract

[reaction: see text] L-Proline-catalyzed direct asymmetric Mannich reactions of N-PMP protected alpha-imino ethyl glyoxylate with various alpha,alpha-disubstituted aldehydes affords quaternary beta-formyl alpha-amino acid derivatives with excellent yields and enantioselectivities. The Mannich products are further converted to the corresponding quaternary alpha- and beta-amino acids and beta-lactams.

Authors+Show Affiliations

Chowdari NS
The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Suri JT
No affiliation info available
Barbas CF
No affiliation info available

MeSH

AldehydesAmino AcidsCatalysisCombinatorial Chemistry TechniquesCrystallography, X-RayMolecular ConformationMolecular StructureProlineStereoisomerismbeta-Lactams

Pub Type(s)

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

Language

eng

PubMed ID

15255677

Citation

Chowdari, Naidu S., et al. "Asymmetric Synthesis of Quaternary Alpha- and Beta-amino Acids and Beta-lactams Via Proline-catalyzed Mannich Reactions With Branched Aldehyde Donors." Organic Letters, vol. 6, no. 15, 2004, pp. 2507-10.
Chowdari NS, Suri JT, Barbas CF. Asymmetric synthesis of quaternary alpha- and beta-amino acids and beta-lactams via proline-catalyzed mannich reactions with branched aldehyde donors. Org Lett. 2004;6(15):2507-10.
Chowdari, N. S., Suri, J. T., & Barbas, C. F. (2004). Asymmetric synthesis of quaternary alpha- and beta-amino acids and beta-lactams via proline-catalyzed mannich reactions with branched aldehyde donors. Organic Letters, 6(15), 2507-10.
Chowdari NS, Suri JT, Barbas CF. Asymmetric Synthesis of Quaternary Alpha- and Beta-amino Acids and Beta-lactams Via Proline-catalyzed Mannich Reactions With Branched Aldehyde Donors. Org Lett. 2004 Jul 22;6(15):2507-10. PubMed PMID: 15255677.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric synthesis of quaternary alpha- and beta-amino acids and beta-lactams via proline-catalyzed mannich reactions with branched aldehyde donors. AU - Chowdari,Naidu S, AU - Suri,Jeff T, AU - Barbas,Carlos F,3rd PY - 2004/7/17/pubmed PY - 2005/2/11/medline PY - 2004/7/17/entrez SP - 2507 EP - 10 JF - Organic letters JO - Org Lett VL - 6 IS - 15 N2 - [reaction: see text] L-Proline-catalyzed direct asymmetric Mannich reactions of N-PMP protected alpha-imino ethyl glyoxylate with various alpha,alpha-disubstituted aldehydes affords quaternary beta-formyl alpha-amino acid derivatives with excellent yields and enantioselectivities. The Mannich products are further converted to the corresponding quaternary alpha- and beta-amino acids and beta-lactams. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/15255677/Asymmetric_synthesis_of_quaternary_alpha__and_beta_amino_acids_and_beta_lactams_via_proline_catalyzed_mannich_reactions_with_branched_aldehyde_donors_ DB - PRIME DP - Unbound Medicine ER -