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Catalytic enantio- and diastereoselective aldol reactions of glycine-derived silicon enolate with aldehydes: an efficient approach to the asymmetric synthesis of anti-beta-hydroxy-alpha-amino acid derivatives.
J Am Chem Soc. 2004 Aug 04; 126(30):9192-3.JA

Abstract

We have developed an efficient method for the asymmetric synthesis of anti-beta-hydroxy-alpha-amino acid derivatives based on highly enantio- and diastereoselective aldol reactions of the silicon enolate derived from N-trifluoroacetylglycinate with aldehydes using a chiral zirconium catalyst. The resulting N-trifluoroacetyl group is easily cleaved under either acidic or basic conditions and can be used directly as a protecting group for further transformations.

Authors+Show Affiliations

Kobayashi J
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Nakamura M
No affiliation info available
Mori Y
No affiliation info available
Yamashita Y
No affiliation info available
Kobayashi S
No affiliation info available

MeSH

AldehydesAmino AcidsCatalysisFluoroacetatesGlycineHydroxy AcidsSiliconStereoisomerismZirconium

Pub Type(s)

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

Language

eng

PubMed ID

15281803

Citation

Kobayashi, Jun, et al. "Catalytic Enantio- and Diastereoselective Aldol Reactions of Glycine-derived Silicon Enolate With Aldehydes: an Efficient Approach to the Asymmetric Synthesis of Anti-beta-hydroxy-alpha-amino Acid Derivatives." Journal of the American Chemical Society, vol. 126, no. 30, 2004, pp. 9192-3.
Kobayashi J, Nakamura M, Mori Y, et al. Catalytic enantio- and diastereoselective aldol reactions of glycine-derived silicon enolate with aldehydes: an efficient approach to the asymmetric synthesis of anti-beta-hydroxy-alpha-amino acid derivatives. J Am Chem Soc. 2004;126(30):9192-3.
Kobayashi, J., Nakamura, M., Mori, Y., Yamashita, Y., & Kobayashi, S. (2004). Catalytic enantio- and diastereoselective aldol reactions of glycine-derived silicon enolate with aldehydes: an efficient approach to the asymmetric synthesis of anti-beta-hydroxy-alpha-amino acid derivatives. Journal of the American Chemical Society, 126(30), 9192-3.
Kobayashi J, et al. Catalytic Enantio- and Diastereoselective Aldol Reactions of Glycine-derived Silicon Enolate With Aldehydes: an Efficient Approach to the Asymmetric Synthesis of Anti-beta-hydroxy-alpha-amino Acid Derivatives. J Am Chem Soc. 2004 Aug 4;126(30):9192-3. PubMed PMID: 15281803.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic enantio- and diastereoselective aldol reactions of glycine-derived silicon enolate with aldehydes: an efficient approach to the asymmetric synthesis of anti-beta-hydroxy-alpha-amino acid derivatives. AU - Kobayashi,Jun, AU - Nakamura,Masayuki, AU - Mori,Yuichiro, AU - Yamashita,Yasuhiro, AU - Kobayashi,Shu, PY - 2004/7/30/pubmed PY - 2004/11/2/medline PY - 2004/7/30/entrez SP - 9192 EP - 3 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 126 IS - 30 N2 - We have developed an efficient method for the asymmetric synthesis of anti-beta-hydroxy-alpha-amino acid derivatives based on highly enantio- and diastereoselective aldol reactions of the silicon enolate derived from N-trifluoroacetylglycinate with aldehydes using a chiral zirconium catalyst. The resulting N-trifluoroacetyl group is easily cleaved under either acidic or basic conditions and can be used directly as a protecting group for further transformations. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/15281803/Catalytic_enantio__and_diastereoselective_aldol_reactions_of_glycine_derived_silicon_enolate_with_aldehydes:_an_efficient_approach_to_the_asymmetric_synthesis_of_anti_beta_hydroxy_alpha_amino_acid_derivatives_ DB - PRIME DP - Unbound Medicine ER -