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Chiral N-phosphonyl imine chemistry: asymmetric synthesis of alpha-alkyl beta-amino ketones by reacting phosphonyl imines with ketone-derived enolates.
Chem Biol Drug Des. 2009 Feb; 73(2):203-8.CB

Abstract

A series of new chiral syn-alpha-branched beta-amino ketones has been synthesized by reacting chiral phosphonyl imines with ketone-derived enolates. The N-protection group on imine auxiliary was found to be crucial to the asymmetric induction. The absolute stereochemistry has been unambiguously determined by converting a product to a known sample.

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Authors+Show Affiliations

Ai T
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79401-1061, USA.
Han J
No affiliation info available
Chen ZX
No affiliation info available
Li G
No affiliation info available

MeSH

IminesKetonesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

19207422

Citation

Ai, Teng, et al. "Chiral N-phosphonyl Imine Chemistry: Asymmetric Synthesis of Alpha-alkyl Beta-amino Ketones By Reacting Phosphonyl Imines With Ketone-derived Enolates." Chemical Biology & Drug Design, vol. 73, no. 2, 2009, pp. 203-8.
Ai T, Han J, Chen ZX, et al. Chiral N-phosphonyl imine chemistry: asymmetric synthesis of alpha-alkyl beta-amino ketones by reacting phosphonyl imines with ketone-derived enolates. Chem Biol Drug Des. 2009;73(2):203-8.
Ai, T., Han, J., Chen, Z. X., & Li, G. (2009). Chiral N-phosphonyl imine chemistry: asymmetric synthesis of alpha-alkyl beta-amino ketones by reacting phosphonyl imines with ketone-derived enolates. Chemical Biology & Drug Design, 73(2), 203-8. https://doi.org/10.1111/j.1747-0285.2008.00771.x
Ai T, et al. Chiral N-phosphonyl Imine Chemistry: Asymmetric Synthesis of Alpha-alkyl Beta-amino Ketones By Reacting Phosphonyl Imines With Ketone-derived Enolates. Chem Biol Drug Des. 2009;73(2):203-8. PubMed PMID: 19207422.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Chiral N-phosphonyl imine chemistry: asymmetric synthesis of alpha-alkyl beta-amino ketones by reacting phosphonyl imines with ketone-derived enolates. AU - Ai,Teng, AU - Han,Jianlin, AU - Chen,Zhong-Xiu, AU - Li,Guigen, PY - 2009/2/12/entrez PY - 2009/2/12/pubmed PY - 2009/4/7/medline SP - 203 EP - 8 JF - Chemical biology & drug design JO - Chem Biol Drug Des VL - 73 IS - 2 N2 - A series of new chiral syn-alpha-branched beta-amino ketones has been synthesized by reacting chiral phosphonyl imines with ketone-derived enolates. The N-protection group on imine auxiliary was found to be crucial to the asymmetric induction. The absolute stereochemistry has been unambiguously determined by converting a product to a known sample. SN - 1747-0285 UR - https://www.unboundmedicine.com/medline/citation/19207422/Chiral_N_phosphonyl_imine_chemistry:_asymmetric_synthesis_of_alpha_alkyl_beta_amino_ketones_by_reacting_phosphonyl_imines_with_ketone_derived_enolates_ L2 - https://doi.org/10.1111/j.1747-0285.2008.00771.x DB - PRIME DP - Unbound Medicine ER -