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Enantioselective addition of ketene silyl acetals to nitrones catalyzed by chiral titanium complexes. Synthesis of optically active beta-amino acids.
J Am Chem Soc. 2002 Mar 27; 124(12):2888-9.JA

Abstract

A chiral titanium complex, Ti(O-i-Pr)(4)/BINOL/tert-butylcatechol, catalyzes enantioselective addition reaction of ketene silyl acetals to nitrones to give optically active beta-amino acid derivatives which are biologically active compounds and useful synthetic intermediates of natural products and pharmaceuticals such as beta-lactam antibiotics. The combined process of catalytic oxidation of secondary amines and enantioselective carbon-carbon bond formation of nitrones thus obtained with ketene silyl acetals provides a useful two-step method for the synthesis of optically active beta-amino acid derivatives and related nitrogen compounds.

Authors+Show Affiliations

Murahashi S
Department of Chemistry, Graduate School of Engineering Science, Osaka University, 1-3 Machikaneyama, Toyonaka, Osaka 560-8531, Japan.
Imada Y
No affiliation info available
Kawakami T
No affiliation info available
Harada K
No affiliation info available
Yonemushi Y
No affiliation info available
Tomita N
No affiliation info available

MeSH

AcetalsAmino AcidsEthylenesKetonesNitrogen OxidesSiliconStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

11902876

Citation

Murahashi, Shun-Ichi, et al. "Enantioselective Addition of Ketene Silyl Acetals to Nitrones Catalyzed By Chiral Titanium Complexes. Synthesis of Optically Active Beta-amino Acids." Journal of the American Chemical Society, vol. 124, no. 12, 2002, pp. 2888-9.
Murahashi S, Imada Y, Kawakami T, et al. Enantioselective addition of ketene silyl acetals to nitrones catalyzed by chiral titanium complexes. Synthesis of optically active beta-amino acids. J Am Chem Soc. 2002;124(12):2888-9.
Murahashi, S., Imada, Y., Kawakami, T., Harada, K., Yonemushi, Y., & Tomita, N. (2002). Enantioselective addition of ketene silyl acetals to nitrones catalyzed by chiral titanium complexes. Synthesis of optically active beta-amino acids. Journal of the American Chemical Society, 124(12), 2888-9.
Murahashi S, et al. Enantioselective Addition of Ketene Silyl Acetals to Nitrones Catalyzed By Chiral Titanium Complexes. Synthesis of Optically Active Beta-amino Acids. J Am Chem Soc. 2002 Mar 27;124(12):2888-9. PubMed PMID: 11902876.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective addition of ketene silyl acetals to nitrones catalyzed by chiral titanium complexes. Synthesis of optically active beta-amino acids. AU - Murahashi,Shun-Ichi, AU - Imada,Yasushi, AU - Kawakami,Toru, AU - Harada,Kazuhito, AU - Yonemushi,Yoshiharu, AU - Tomita,Naomi, PY - 2002/3/21/pubmed PY - 2002/6/5/medline PY - 2002/3/21/entrez SP - 2888 EP - 9 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 124 IS - 12 N2 - A chiral titanium complex, Ti(O-i-Pr)(4)/BINOL/tert-butylcatechol, catalyzes enantioselective addition reaction of ketene silyl acetals to nitrones to give optically active beta-amino acid derivatives which are biologically active compounds and useful synthetic intermediates of natural products and pharmaceuticals such as beta-lactam antibiotics. The combined process of catalytic oxidation of secondary amines and enantioselective carbon-carbon bond formation of nitrones thus obtained with ketene silyl acetals provides a useful two-step method for the synthesis of optically active beta-amino acid derivatives and related nitrogen compounds. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/11902876/Enantioselective_addition_of_ketene_silyl_acetals_to_nitrones_catalyzed_by_chiral_titanium_complexes__Synthesis_of_optically_active_beta_amino_acids_ L2 - https://doi.org/10.1021/ja0176649 DB - PRIME DP - Unbound Medicine ER -