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Highly diastereoselective Michael addition reactions of butane-2,3-diacetal desymmetrized glycolic acid. Preparation of alpha-hydroxy-gamma-amino acid derivatives.
Org Lett. 2001 Nov 15; 3(23):3753-5.OL

Abstract

[reaction--see text] The butane-2,3-diacetal (BDA) desymmetrized glycolic acid building block undergoes efficient and highly diastereoselective lithium enolate Michael additions to alpha,beta-unsaturated ketones, lactones, and nitro olefins. Subsequent deprotection of these Michael adducts gives alpha-hydroxy acids in very high yield. Hydrogenation of the nitro group in some of the adducts leads to gamma-lactams, which can be easily converted into alpha-hydroxy-gamma-amino acid derivatives.

Authors+Show Affiliations

Dixon DJ
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK. .
Ley SV
No affiliation info available
Rodríguez F
No affiliation info available

MeSH

AcetalsCatalysisIndicators and ReagentsLithiumLithium CompoundsMagnetic Resonance SpectroscopySilanes

Pub Type(s)

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

Language

eng

PubMed ID

11700130

Citation

Dixon, D J., et al. "Highly Diastereoselective Michael Addition Reactions of Butane-2,3-diacetal Desymmetrized Glycolic Acid. Preparation of Alpha-hydroxy-gamma-amino Acid Derivatives." Organic Letters, vol. 3, no. 23, 2001, pp. 3753-5.
Dixon DJ, Ley SV, Rodríguez F. Highly diastereoselective Michael addition reactions of butane-2,3-diacetal desymmetrized glycolic acid. Preparation of alpha-hydroxy-gamma-amino acid derivatives. Org Lett. 2001;3(23):3753-5.
Dixon, D. J., Ley, S. V., & Rodríguez, F. (2001). Highly diastereoselective Michael addition reactions of butane-2,3-diacetal desymmetrized glycolic acid. Preparation of alpha-hydroxy-gamma-amino acid derivatives. Organic Letters, 3(23), 3753-5.
Dixon DJ, Ley SV, Rodríguez F. Highly Diastereoselective Michael Addition Reactions of Butane-2,3-diacetal Desymmetrized Glycolic Acid. Preparation of Alpha-hydroxy-gamma-amino Acid Derivatives. Org Lett. 2001 Nov 15;3(23):3753-5. PubMed PMID: 11700130.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly diastereoselective Michael addition reactions of butane-2,3-diacetal desymmetrized glycolic acid. Preparation of alpha-hydroxy-gamma-amino acid derivatives. AU - Dixon,D J, AU - Ley,S V, AU - Rodríguez,F, PY - 2001/11/9/pubmed PY - 2002/1/5/medline PY - 2001/11/9/entrez SP - 3753 EP - 5 JF - Organic letters JO - Org Lett VL - 3 IS - 23 N2 - [reaction--see text] The butane-2,3-diacetal (BDA) desymmetrized glycolic acid building block undergoes efficient and highly diastereoselective lithium enolate Michael additions to alpha,beta-unsaturated ketones, lactones, and nitro olefins. Subsequent deprotection of these Michael adducts gives alpha-hydroxy acids in very high yield. Hydrogenation of the nitro group in some of the adducts leads to gamma-lactams, which can be easily converted into alpha-hydroxy-gamma-amino acid derivatives. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/11700130/Highly_diastereoselective_Michael_addition_reactions_of_butane_23_diacetal_desymmetrized_glycolic_acid__Preparation_of_alpha_hydroxy_gamma_amino_acid_derivatives_ L2 - https://doi.org/10.1021/ol016708f DB - PRIME DP - Unbound Medicine ER -