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Direct organocatalytic asymmetric aldol reactions of alpha-amino aldehydes: expedient syntheses of highly enantiomerically enriched anti-beta-hydroxy-alpha-amino acids.
Org Lett. 2004 Sep 30; 6(20):3541-4.OL

Abstract

[reaction: see text] A simple and efficient method for the synthesis of highly enantiomerically enriched beta-hydroxy-alpha-amino acid derivatives has been developed. Direct asymmetric aldol reactions of a glycine aldehyde (aminoacetaldehyde) derivative have been performed under organocatalysis using l-proline or (S)-5-pyrrolidine-2-yl-1H-tetrazole. The reactions afforded anti-beta-hydroxy-alpha-amino aldehydes in good yield with high diastereoselectivity (dr up to >100:1) and high enantioselectivity (up to >99.5% ee), which were easily transformed into beta-hydroxy-alpha-amino acid derivatives.

Authors+Show Affiliations

Thayumanavan R
Department of Chemistry and Molecular Biology and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Tanaka F
No affiliation info available
Barbas III CF
No affiliation info available

MeSH

AldehydesAmino AcidsCatalysisIndicators and ReagentsMolecular StructureProlineStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

15387543

Citation

Thayumanavan, Rajeswari, et al. "Direct Organocatalytic Asymmetric Aldol Reactions of Alpha-amino Aldehydes: Expedient Syntheses of Highly Enantiomerically Enriched Anti-beta-hydroxy-alpha-amino Acids." Organic Letters, vol. 6, no. 20, 2004, pp. 3541-4.
Thayumanavan R, Tanaka F, Barbas III CF. Direct organocatalytic asymmetric aldol reactions of alpha-amino aldehydes: expedient syntheses of highly enantiomerically enriched anti-beta-hydroxy-alpha-amino acids. Org Lett. 2004;6(20):3541-4.
Thayumanavan, R., Tanaka, F., & Barbas III, C. F. (2004). Direct organocatalytic asymmetric aldol reactions of alpha-amino aldehydes: expedient syntheses of highly enantiomerically enriched anti-beta-hydroxy-alpha-amino acids. Organic Letters, 6(20), 3541-4.
Thayumanavan R, Tanaka F, Barbas III CF. Direct Organocatalytic Asymmetric Aldol Reactions of Alpha-amino Aldehydes: Expedient Syntheses of Highly Enantiomerically Enriched Anti-beta-hydroxy-alpha-amino Acids. Org Lett. 2004 Sep 30;6(20):3541-4. PubMed PMID: 15387543.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Direct organocatalytic asymmetric aldol reactions of alpha-amino aldehydes: expedient syntheses of highly enantiomerically enriched anti-beta-hydroxy-alpha-amino acids. AU - Thayumanavan,Rajeswari, AU - Tanaka,Fujie, AU - Barbas III,Carlos F, PY - 2004/9/25/pubmed PY - 2005/11/1/medline PY - 2004/9/25/entrez SP - 3541 EP - 4 JF - Organic letters JO - Org Lett VL - 6 IS - 20 N2 - [reaction: see text] A simple and efficient method for the synthesis of highly enantiomerically enriched beta-hydroxy-alpha-amino acid derivatives has been developed. Direct asymmetric aldol reactions of a glycine aldehyde (aminoacetaldehyde) derivative have been performed under organocatalysis using l-proline or (S)-5-pyrrolidine-2-yl-1H-tetrazole. The reactions afforded anti-beta-hydroxy-alpha-amino aldehydes in good yield with high diastereoselectivity (dr up to >100:1) and high enantioselectivity (up to >99.5% ee), which were easily transformed into beta-hydroxy-alpha-amino acid derivatives. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/15387543/Direct_organocatalytic_asymmetric_aldol_reactions_of_alpha_amino_aldehydes:_expedient_syntheses_of_highly_enantiomerically_enriched_anti_beta_hydroxy_alpha_amino_acids_ DB - PRIME DP - Unbound Medicine ER -
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