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An efficient dipeptide-catalyzed direct asymmetric aldol reaction of equimolar reactants in solid media.
Chirality. 2010 Jun; 22(6):580-6.C

Abstract

The direct asymmetric aldol reactions of equivalent molar amounts of aldehydes and ketones were carried out at -20 degrees C over alkaline Al(2)O(3) with 20 mol % of Pro-Trp as catalyst and 20 mol % of N-methylmorpholine or 1,4-diazabicyclo[2.2.2]octane as additive. After simple and environmentally friendly work-up, moderate to high isolated yields (up to 95%), good diastereoselectivities (>99:1), and enantioselectivities (up to 98% ee) have been achieved for the reactions of different kinds of ketones with various aldehydes. The catalytic system could be reused without decrease of activity by addition of 10 mol % catalyst and base in the catalytic system.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Lei M
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, China.
Xia S
No affiliation info available
Wang J
No affiliation info available
Ge Z
No affiliation info available
Cheng T
No affiliation info available
Li R
No affiliation info available

MeSH

AldehydesAluminum OxideCatalysisDipeptidesKetones

Pub Type(s)

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

Language

eng

PubMed ID

19899160

Citation

Lei, Meng, et al. "An Efficient Dipeptide-catalyzed Direct Asymmetric Aldol Reaction of Equimolar Reactants in Solid Media." Chirality, vol. 22, no. 6, 2010, pp. 580-6.
Lei M, Xia S, Wang J, et al. An efficient dipeptide-catalyzed direct asymmetric aldol reaction of equimolar reactants in solid media. Chirality. 2010;22(6):580-6.
Lei, M., Xia, S., Wang, J., Ge, Z., Cheng, T., & Li, R. (2010). An efficient dipeptide-catalyzed direct asymmetric aldol reaction of equimolar reactants in solid media. Chirality, 22(6), 580-6. https://doi.org/10.1002/chir.20783
Lei M, et al. An Efficient Dipeptide-catalyzed Direct Asymmetric Aldol Reaction of Equimolar Reactants in Solid Media. Chirality. 2010;22(6):580-6. PubMed PMID: 19899160.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - An efficient dipeptide-catalyzed direct asymmetric aldol reaction of equimolar reactants in solid media. AU - Lei,Meng, AU - Xia,Shuai, AU - Wang,Junfeng, AU - Ge,Zemei, AU - Cheng,Tieming, AU - Li,Runtao, PY - 2009/11/10/entrez PY - 2009/11/10/pubmed PY - 2010/8/21/medline SP - 580 EP - 6 JF - Chirality JO - Chirality VL - 22 IS - 6 N2 - The direct asymmetric aldol reactions of equivalent molar amounts of aldehydes and ketones were carried out at -20 degrees C over alkaline Al(2)O(3) with 20 mol % of Pro-Trp as catalyst and 20 mol % of N-methylmorpholine or 1,4-diazabicyclo[2.2.2]octane as additive. After simple and environmentally friendly work-up, moderate to high isolated yields (up to 95%), good diastereoselectivities (>99:1), and enantioselectivities (up to 98% ee) have been achieved for the reactions of different kinds of ketones with various aldehydes. The catalytic system could be reused without decrease of activity by addition of 10 mol % catalyst and base in the catalytic system. SN - 1520-636X UR - https://www.unboundmedicine.com/medline/citation/19899160/An_efficient_dipeptide_catalyzed_direct_asymmetric_aldol_reaction_of_equimolar_reactants_in_solid_media_ L2 - https://doi.org/10.1002/chir.20783 DB - PRIME DP - Unbound Medicine ER -