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Molecular recognition of ketomalonates by asymmetric aldol reaction of aldehydes with secondary-amine organocatalysts.
Chem Commun (Camb). 2012 Jul 18; 48(56):7037-9.CC

Abstract

A diastereo- and enantioselective aldol reaction between aldehydes and a synthetically useful ketomalonate 1c as a hydrated form was developed, and either anti- or syn-aldol adducts having a chiral tetrasubstituted carbon center were obtained in high enantioselectivities by use of a tetrazole analogue of L-proline (S)-2 or an axially chiral amino sulfonamide (S)-3 as catalyst.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Kano T
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.
Song S
No affiliation info available
Maruoka K
No affiliation info available

MeSH

AldehydesAminesCatalysisMalonatesMolecular StructureStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

22684237

Citation

Kano, Taichi, et al. "Molecular Recognition of Ketomalonates By Asymmetric Aldol Reaction of Aldehydes With Secondary-amine Organocatalysts." Chemical Communications (Cambridge, England), vol. 48, no. 56, 2012, pp. 7037-9.
Kano T, Song S, Maruoka K. Molecular recognition of ketomalonates by asymmetric aldol reaction of aldehydes with secondary-amine organocatalysts. Chem Commun (Camb). 2012;48(56):7037-9.
Kano, T., Song, S., & Maruoka, K. (2012). Molecular recognition of ketomalonates by asymmetric aldol reaction of aldehydes with secondary-amine organocatalysts. Chemical Communications (Cambridge, England), 48(56), 7037-9. https://doi.org/10.1039/c2cc32772d
Kano T, Song S, Maruoka K. Molecular Recognition of Ketomalonates By Asymmetric Aldol Reaction of Aldehydes With Secondary-amine Organocatalysts. Chem Commun (Camb). 2012 Jul 18;48(56):7037-9. PubMed PMID: 22684237.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Molecular recognition of ketomalonates by asymmetric aldol reaction of aldehydes with secondary-amine organocatalysts. AU - Kano,Taichi, AU - Song,Sunhwa, AU - Maruoka,Keiji, Y1 - 2012/06/11/ PY - 2012/6/12/entrez PY - 2012/6/12/pubmed PY - 2012/10/12/medline SP - 7037 EP - 9 JF - Chemical communications (Cambridge, England) JO - Chem Commun (Camb) VL - 48 IS - 56 N2 - A diastereo- and enantioselective aldol reaction between aldehydes and a synthetically useful ketomalonate 1c as a hydrated form was developed, and either anti- or syn-aldol adducts having a chiral tetrasubstituted carbon center were obtained in high enantioselectivities by use of a tetrazole analogue of L-proline (S)-2 or an axially chiral amino sulfonamide (S)-3 as catalyst. SN - 1364-548X UR - https://www.unboundmedicine.com/medline/citation/22684237/Molecular_recognition_of_ketomalonates_by_asymmetric_aldol_reaction_of_aldehydes_with_secondary_amine_organocatalysts_ L2 - https://doi.org/10.1039/c2cc32772d DB - PRIME DP - Unbound Medicine ER -