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Double stereodifferentiation in the "acetate-type" aldol reaction with garner's aldehyde. Stereocontrolled synthesis of polyhydroxylated gamma-amino carbonyl compounds.
Org Lett. 2004 Sep 02; 6(18):3171-4.OL

Abstract

[reaction: see text] The aldol reaction of acetamide enolates with protected chiral alpha-amino-beta-hydroxy aldehyde 1 (Garner's aldehyde) has been performed in a stereocontrolled way under double stereodifferentiation conditions using pseudoephedrine as the additional chiral information source attached to the enolate reagent. In addition, the obtained adduct has been transformed into other valuable chiral building blocks such as gamma-amino-beta,delta-dihydroxy acids, esters, and ketones.

Authors+Show Affiliations

Vicario JL
Departamento de Química Orgánica II, Facultad de Ciencias, Universidad del País Vasco-Euskal Herriko Unibertsitatea, P.O. Box E-644, 48080 Bilbao, Spain.
Rodriguez M
No affiliation info available
Badía D
No affiliation info available
Carrillo L
No affiliation info available
Reyes E
No affiliation info available

MeSH

AcetatesAldehydesAminesCatalysisEphedrineHydroxy AcidsIndicators and ReagentsKetonesMolecular StructureStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

15330615

Citation

Vicario, Jose L., et al. "Double Stereodifferentiation in the "acetate-type" Aldol Reaction With Garner's Aldehyde. Stereocontrolled Synthesis of Polyhydroxylated Gamma-amino Carbonyl Compounds." Organic Letters, vol. 6, no. 18, 2004, pp. 3171-4.
Vicario JL, Rodriguez M, Badía D, et al. Double stereodifferentiation in the "acetate-type" aldol reaction with garner's aldehyde. Stereocontrolled synthesis of polyhydroxylated gamma-amino carbonyl compounds. Org Lett. 2004;6(18):3171-4.
Vicario, J. L., Rodriguez, M., Badía, D., Carrillo, L., & Reyes, E. (2004). Double stereodifferentiation in the "acetate-type" aldol reaction with garner's aldehyde. Stereocontrolled synthesis of polyhydroxylated gamma-amino carbonyl compounds. Organic Letters, 6(18), 3171-4.
Vicario JL, et al. Double Stereodifferentiation in the "acetate-type" Aldol Reaction With Garner's Aldehyde. Stereocontrolled Synthesis of Polyhydroxylated Gamma-amino Carbonyl Compounds. Org Lett. 2004 Sep 2;6(18):3171-4. PubMed PMID: 15330615.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Double stereodifferentiation in the "acetate-type" aldol reaction with garner's aldehyde. Stereocontrolled synthesis of polyhydroxylated gamma-amino carbonyl compounds. AU - Vicario,Jose L, AU - Rodriguez,Mónica, AU - Badía,Dolores, AU - Carrillo,Luisa, AU - Reyes,Efraim, PY - 2004/8/28/pubmed PY - 2005/9/22/medline PY - 2004/8/28/entrez SP - 3171 EP - 4 JF - Organic letters JO - Org Lett VL - 6 IS - 18 N2 - [reaction: see text] The aldol reaction of acetamide enolates with protected chiral alpha-amino-beta-hydroxy aldehyde 1 (Garner's aldehyde) has been performed in a stereocontrolled way under double stereodifferentiation conditions using pseudoephedrine as the additional chiral information source attached to the enolate reagent. In addition, the obtained adduct has been transformed into other valuable chiral building blocks such as gamma-amino-beta,delta-dihydroxy acids, esters, and ketones. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/15330615/Double_stereodifferentiation_in_the_"acetate_type"_aldol_reaction_with_garner's_aldehyde__Stereocontrolled_synthesis_of_polyhydroxylated_gamma_amino_carbonyl_compounds_ DB - PRIME DP - Unbound Medicine ER -