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Green asymmetric synthesis: β-amino alcohol-catalyzed direct asymmetric aldol reactions in aqueous micelles.
Chirality. 2013 Feb; 25(2):119-25.C

Abstract

The ability of chiral β-amino alcohols to catalyze the direct asymmetric aldol reaction was evaluated for the first time in aqueous micellar media. A family of cheap and easily accessible β-amino alcohols, obtained in one step from naturally occurring amino acids, was shown to successfully catalyze the asymmetric aldol reaction between a series of ketones and aromatic aldehydes. These aldol reactions furnished the corresponding β-hydroxy ketones with up to 93% isolated yield and 89% ee. (S)-2-phenylglycinol and Triton X-100 proved to be the best organocatalyst and surfactant, respectively.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Pinaka A
Institute of Physical Chemistry, NCSR Demokritos, 15310, Athens, Greece.
Vougioukalakis GC
No affiliation info available
Dimotikali D
No affiliation info available
Yannakopoulou E
No affiliation info available
Chankvetadze B
No affiliation info available
Papadopoulos K
No affiliation info available

MeSH

AldehydesAmino AlcoholsCatalysisChemistry Techniques, SyntheticGreen Chemistry TechnologyKetonesMicellesWater

Pub Type(s)

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

Language

eng

PubMed ID

23192785

Citation

Pinaka, Afroditi, et al. "Green Asymmetric Synthesis: Β-amino Alcohol-catalyzed Direct Asymmetric Aldol Reactions in Aqueous Micelles." Chirality, vol. 25, no. 2, 2013, pp. 119-25.
Pinaka A, Vougioukalakis GC, Dimotikali D, et al. Green asymmetric synthesis: β-amino alcohol-catalyzed direct asymmetric aldol reactions in aqueous micelles. Chirality. 2013;25(2):119-25.
Pinaka, A., Vougioukalakis, G. C., Dimotikali, D., Yannakopoulou, E., Chankvetadze, B., & Papadopoulos, K. (2013). Green asymmetric synthesis: β-amino alcohol-catalyzed direct asymmetric aldol reactions in aqueous micelles. Chirality, 25(2), 119-25. https://doi.org/10.1002/chir.22120
Pinaka A, et al. Green Asymmetric Synthesis: Β-amino Alcohol-catalyzed Direct Asymmetric Aldol Reactions in Aqueous Micelles. Chirality. 2013;25(2):119-25. PubMed PMID: 23192785.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Green asymmetric synthesis: β-amino alcohol-catalyzed direct asymmetric aldol reactions in aqueous micelles. AU - Pinaka,Afroditi, AU - Vougioukalakis,Georgios C, AU - Dimotikali,Dimitra, AU - Yannakopoulou,Elina, AU - Chankvetadze,Bezhan, AU - Papadopoulos,Kyriakos, Y1 - 2012/11/28/ PY - 2012/06/23/received PY - 2012/09/21/accepted PY - 2012/11/30/entrez PY - 2012/11/30/pubmed PY - 2013/12/18/medline SP - 119 EP - 25 JF - Chirality JO - Chirality VL - 25 IS - 2 N2 - The ability of chiral β-amino alcohols to catalyze the direct asymmetric aldol reaction was evaluated for the first time in aqueous micellar media. A family of cheap and easily accessible β-amino alcohols, obtained in one step from naturally occurring amino acids, was shown to successfully catalyze the asymmetric aldol reaction between a series of ketones and aromatic aldehydes. These aldol reactions furnished the corresponding β-hydroxy ketones with up to 93% isolated yield and 89% ee. (S)-2-phenylglycinol and Triton X-100 proved to be the best organocatalyst and surfactant, respectively. SN - 1520-636X UR - https://www.unboundmedicine.com/medline/citation/23192785/Green_asymmetric_synthesis:_β_amino_alcohol_catalyzed_direct_asymmetric_aldol_reactions_in_aqueous_micelles_ L2 - https://doi.org/10.1002/chir.22120 DB - PRIME DP - Unbound Medicine ER -