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Proline-catalyzed diastereoselective direct aldol reaction between 4-oxoazetidine-2-carbaldehydes and ketones.
J Org Chem. 2006 Jun 23; 71(13):4818-22.JO

Abstract

The reaction of enantiopure 4-oxoazetidine-2-carbaldehydes with unmodified ketones was catalyzed by L-proline as well as by D-proline, to give the corresponding gamma-amino-beta-hydroxy ketones with good yields and diastereoselectivities. The obtained results implied that (2R,3R)-4-oxoazetidine-2-carbaldehydes and L-proline are a matched pair for diastereoselective induction.

Authors+Show Affiliations

Alcaide B
Departamento de Química Organica I, Facultad de Química, Universidad Complutense de Madrid, 28040 Madrid, Spain. alcaideb@quim.ucm.es
Almendros P
No affiliation info available
Luna A
No affiliation info available
Torres MR
No affiliation info available

MeSH

AldehydesAzetidinesCatalysisKetonesMolecular ConformationProlineStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

16776507

Citation

Alcaide, Benito, et al. "Proline-catalyzed Diastereoselective Direct Aldol Reaction Between 4-oxoazetidine-2-carbaldehydes and Ketones." The Journal of Organic Chemistry, vol. 71, no. 13, 2006, pp. 4818-22.
Alcaide B, Almendros P, Luna A, et al. Proline-catalyzed diastereoselective direct aldol reaction between 4-oxoazetidine-2-carbaldehydes and ketones. J Org Chem. 2006;71(13):4818-22.
Alcaide, B., Almendros, P., Luna, A., & Torres, M. R. (2006). Proline-catalyzed diastereoselective direct aldol reaction between 4-oxoazetidine-2-carbaldehydes and ketones. The Journal of Organic Chemistry, 71(13), 4818-22.
Alcaide B, et al. Proline-catalyzed Diastereoselective Direct Aldol Reaction Between 4-oxoazetidine-2-carbaldehydes and Ketones. J Org Chem. 2006 Jun 23;71(13):4818-22. PubMed PMID: 16776507.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Proline-catalyzed diastereoselective direct aldol reaction between 4-oxoazetidine-2-carbaldehydes and ketones. AU - Alcaide,Benito, AU - Almendros,Pedro, AU - Luna,Amparo, AU - Torres,M Rosario, PY - 2006/6/17/pubmed PY - 2007/6/28/medline PY - 2006/6/17/entrez SP - 4818 EP - 22 JF - The Journal of organic chemistry JO - J Org Chem VL - 71 IS - 13 N2 - The reaction of enantiopure 4-oxoazetidine-2-carbaldehydes with unmodified ketones was catalyzed by L-proline as well as by D-proline, to give the corresponding gamma-amino-beta-hydroxy ketones with good yields and diastereoselectivities. The obtained results implied that (2R,3R)-4-oxoazetidine-2-carbaldehydes and L-proline are a matched pair for diastereoselective induction. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/16776507/Proline_catalyzed_diastereoselective_direct_aldol_reaction_between_4_oxoazetidine_2_carbaldehydes_and_ketones_ DB - PRIME DP - Unbound Medicine ER -