Asymmetric synthesis of β-hydroxy amino acids via aldol reactions catalyzed by chiral ammonium salts

Journal of Organic Chemistry

Volumn 69, Issue 19, 2004, Pages 6489-6492

  Mettath, Sashikumar ^a   Srikanth, G S C ^a   Dangerfield, Benjamin S ^a   Castle, Steven L ^a  

^a BRIGHAM YOUNG UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM COMPOUNDS; CATALYSTS; SALTS; STEREOCHEMISTRY; SUBSTRATES; SYNTHESIS (CHEMICAL);

ALDOL REACTIONS; CHIRAL AMMONIUM SALTS; DIASTEREOMERS; HOMOGENEITY;

AMINO ACIDS;

ALDEHYDE DERIVATIVE; ALIPHATIC COMPOUND; AMINO ACID DERIVATIVE; AMMONIUM DERIVATIVE; CINCHONA ALKALOID; GLYCINE; HYDROXYAMINO ACID; SCHIFF BASE;

ACYLATION; ALDOL REACTION; AMINO ACID SYNTHESIS; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; ENANTIOSELECTIVITY; HYDROLYSIS; PROTEIN STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REPRODUCIBILITY; STEREOCHEMISTRY; STOICHIOMETRY; TECHNIQUE;

ALDEHYDES; AMINO ACIDS; CATALYSIS; MAGNETIC RESONANCE SPECTROSCOPY; QUATERNARY AMMONIUM COMPOUNDS; SALTS; STEREOISOMERISM;

EID: 4644225375     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049283u     Document Type: Article

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49. We were unable to isolate anti-11 from the byproducts of hydrolysis and the competing retro aldol reaction. Thus, the 16% yield represents an upper limit. However, our sample was of sufficient purity to determine the ee using chiral HPLC (Chiralcel OD-H, 98:2 hexanes/ i-PrOH, 1 mL/min).
50. 2 chromatography; as detailed above, we were unable to perform this separation in our system. For a discussion of the possible source of these discrepancies, please see footnote 21.
51. We speculate that the presence of the phosphazene base in the crude reaction mixture may be initiating the retro aldol reaction on silica gel. In the aldol reactions reported by Molinski,3a base is presumably not present in the mixture at the time of chromatography and therefore is unable to promote a retro aldol reaction. Thus, we are currently examining the use of other bases that can be removed prior to chromatography in order to extend the substrate scope to aryl aldehydes.
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