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Development of highly diastereo- and enantioselective direct asymmetric aldol reaction of a glycinate Schiff base with aldehydes catalyzed by chiral quaternary ammonium salts.
J Am Chem Soc. 2004 Aug 11; 126(31):9685-94.JA

Abstract

A highly efficient direct asymmetric aldol reaction of a glycinate Schiff base with aldehydes has been achieved under mild organic/aqueous biphasic conditions with excellent stereochemical control, using chiral quaternary ammonium salt 1b as a phase-transfer catalyst. The initially developed reaction conditions, using 2 equiv of aqueous base (1% NaOH (aq)), exhibited inexplicably limited general applicability in terms of aldehyde acceptors. The mechanistic investigation revealed the intervention of an unfavorable yet inevitable retro aldol process involving the chiral catalyst. On the basis of this information, a reliable procedure has been established by use of a catalytic amount of 1% NaOH (aq) and ammonium chloride, which tolerates a wide range of aldehydes to afford the corresponding anti-beta-hydroxy-alpha-amino esters almost exclusively in an essentially optically pure form.

Authors+Show Affiliations

Ooi T
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.
Kameda M
No affiliation info available
Taniguchi M
No affiliation info available
Maruoka K
No affiliation info available

MeSH

AldehydesAmino AcidsCatalysisEstersGlycineQuaternary Ammonium CompoundsSchiff BasesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

15291572

Citation

Ooi, Takashi, et al. "Development of Highly Diastereo- and Enantioselective Direct Asymmetric Aldol Reaction of a Glycinate Schiff Base With Aldehydes Catalyzed By Chiral Quaternary Ammonium Salts." Journal of the American Chemical Society, vol. 126, no. 31, 2004, pp. 9685-94.
Ooi T, Kameda M, Taniguchi M, et al. Development of highly diastereo- and enantioselective direct asymmetric aldol reaction of a glycinate Schiff base with aldehydes catalyzed by chiral quaternary ammonium salts. J Am Chem Soc. 2004;126(31):9685-94.
Ooi, T., Kameda, M., Taniguchi, M., & Maruoka, K. (2004). Development of highly diastereo- and enantioselective direct asymmetric aldol reaction of a glycinate Schiff base with aldehydes catalyzed by chiral quaternary ammonium salts. Journal of the American Chemical Society, 126(31), 9685-94.
Ooi T, et al. Development of Highly Diastereo- and Enantioselective Direct Asymmetric Aldol Reaction of a Glycinate Schiff Base With Aldehydes Catalyzed By Chiral Quaternary Ammonium Salts. J Am Chem Soc. 2004 Aug 11;126(31):9685-94. PubMed PMID: 15291572.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Development of highly diastereo- and enantioselective direct asymmetric aldol reaction of a glycinate Schiff base with aldehydes catalyzed by chiral quaternary ammonium salts. AU - Ooi,Takashi, AU - Kameda,Minoru, AU - Taniguchi,Mika, AU - Maruoka,Keiji, PY - 2004/8/5/pubmed PY - 2004/10/16/medline PY - 2004/8/5/entrez SP - 9685 EP - 94 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 126 IS - 31 N2 - A highly efficient direct asymmetric aldol reaction of a glycinate Schiff base with aldehydes has been achieved under mild organic/aqueous biphasic conditions with excellent stereochemical control, using chiral quaternary ammonium salt 1b as a phase-transfer catalyst. The initially developed reaction conditions, using 2 equiv of aqueous base (1% NaOH (aq)), exhibited inexplicably limited general applicability in terms of aldehyde acceptors. The mechanistic investigation revealed the intervention of an unfavorable yet inevitable retro aldol process involving the chiral catalyst. On the basis of this information, a reliable procedure has been established by use of a catalytic amount of 1% NaOH (aq) and ammonium chloride, which tolerates a wide range of aldehydes to afford the corresponding anti-beta-hydroxy-alpha-amino esters almost exclusively in an essentially optically pure form. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/15291572/Development_of_highly_diastereo__and_enantioselective_direct_asymmetric_aldol_reaction_of_a_glycinate_Schiff_base_with_aldehydes_catalyzed_by_chiral_quaternary_ammonium_salts_ DB - PRIME DP - Unbound Medicine ER -