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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.

Authors+Show Affiliations

Institute of Physical Chemistry, NCSR Demokritos, 15310, Athens, Greece.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

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 -