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The mimic of type II aldolases chemistry: asymmetric synthesis of beta-hydroxy ketones by direct aldol reaction.
Chem Biol Drug Des. 2010 Aug; 76(2):181-6.CB

Abstract

An efficient direct aldol reaction has been developed for the synthesis of chiral beta-hydroxy ketone using a combination of C(1)-symmetric chiral prolinamides based on o-phenylenediamine and zinc triflate as catalyst. The reaction was convenient to carry out in aqueous media with up to 98% chemical yields and up to 94% ee values. The current strategy can be regarded as the analogue of aldolase type II, which suggests a new pathway for the designing of new organocatalysts.

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Authors+Show Affiliations

Lu Z
School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China.
Mei H
No affiliation info available
Han J
No affiliation info available
Pan Y
No affiliation info available

MeSH

BenzaldehydesCatalysisCyclohexanonesFructose-Bisphosphate AldolaseKetonesMesylatesPhenylenediaminesProlineStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

20572810

Citation

Lu, Zhijin, et al. "The Mimic of Type II Aldolases Chemistry: Asymmetric Synthesis of Beta-hydroxy Ketones By Direct Aldol Reaction." Chemical Biology & Drug Design, vol. 76, no. 2, 2010, pp. 181-6.
Lu Z, Mei H, Han J, et al. The mimic of type II aldolases chemistry: asymmetric synthesis of beta-hydroxy ketones by direct aldol reaction. Chem Biol Drug Des. 2010;76(2):181-6.
Lu, Z., Mei, H., Han, J., & Pan, Y. (2010). The mimic of type II aldolases chemistry: asymmetric synthesis of beta-hydroxy ketones by direct aldol reaction. Chemical Biology & Drug Design, 76(2), 181-6. https://doi.org/10.1111/j.1747-0285.2010.00998.x
Lu Z, et al. The Mimic of Type II Aldolases Chemistry: Asymmetric Synthesis of Beta-hydroxy Ketones By Direct Aldol Reaction. Chem Biol Drug Des. 2010;76(2):181-6. PubMed PMID: 20572810.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - The mimic of type II aldolases chemistry: asymmetric synthesis of beta-hydroxy ketones by direct aldol reaction. AU - Lu,Zhijin, AU - Mei,Haibo, AU - Han,Jianlin, AU - Pan,Yi, Y1 - 2010/06/21/ PY - 2010/6/25/entrez PY - 2010/6/25/pubmed PY - 2010/10/22/medline SP - 181 EP - 6 JF - Chemical biology & drug design JO - Chem Biol Drug Des VL - 76 IS - 2 N2 - An efficient direct aldol reaction has been developed for the synthesis of chiral beta-hydroxy ketone using a combination of C(1)-symmetric chiral prolinamides based on o-phenylenediamine and zinc triflate as catalyst. The reaction was convenient to carry out in aqueous media with up to 98% chemical yields and up to 94% ee values. The current strategy can be regarded as the analogue of aldolase type II, which suggests a new pathway for the designing of new organocatalysts. SN - 1747-0285 UR - https://www.unboundmedicine.com/medline/citation/20572810/The_mimic_of_type_II_aldolases_chemistry:_asymmetric_synthesis_of_beta_hydroxy_ketones_by_direct_aldol_reaction_ L2 - https://doi.org/10.1111/j.1747-0285.2010.00998.x DB - PRIME DP - Unbound Medicine ER -