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Direct asymmetric aldol reactions inspired by two types of natural aldolases: water-compatible organocatalysts and Zn(II) complexes.
J Org Chem. 2012 Jan 06; 77(1):173-87.JO

Abstract

In this article the utility of water-compatible amino-acid-based catalysts was explored in the development of diastereo- and enantioselective direct aldol reactions of a broad range of substrates. Chiral C(2)-symmetrical proline- and valine-based amides and their Zn(II) complexes were designed for use as efficient and flexible chiral catalysts for enantioselective aldol reactions in water, on water, and in the presence of water. The presence of 5 mol % of the prolinamide-based catalyst affords asymmetric intermolecular aldol reactions between unmodified ketones and various aldehydes to give anti products with excellent enantioselectivities. We also demonstrate aldol reactions of more demanding substrates with high affinity to water (i.e., acetone and formaldehyde). Newly designed serine-based organocatalyst promoted aldol reaction of hydroxyacetone leading to syn-diols. For presented catalytic systems organic solvent-free conditions are also acceptable, making the elaborated methodology interesting from a green chemistry perspectives.

Authors+Show Affiliations

Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.No 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

22136201

Citation

Paradowska, Joanna, et al. "Direct Asymmetric Aldol Reactions Inspired By Two Types of Natural Aldolases: Water-compatible Organocatalysts and Zn(II) Complexes." The Journal of Organic Chemistry, vol. 77, no. 1, 2012, pp. 173-87.
Paradowska J, Pasternak M, Gut B, et al. Direct asymmetric aldol reactions inspired by two types of natural aldolases: water-compatible organocatalysts and Zn(II) complexes. J Org Chem. 2012;77(1):173-87.
Paradowska, J., Pasternak, M., Gut, B., Gryzło, B., & Mlynarski, J. (2012). Direct asymmetric aldol reactions inspired by two types of natural aldolases: water-compatible organocatalysts and Zn(II) complexes. The Journal of Organic Chemistry, 77(1), 173-87. https://doi.org/10.1021/jo201584w
Paradowska J, et al. Direct Asymmetric Aldol Reactions Inspired By Two Types of Natural Aldolases: Water-compatible Organocatalysts and Zn(II) Complexes. J Org Chem. 2012 Jan 6;77(1):173-87. PubMed PMID: 22136201.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Direct asymmetric aldol reactions inspired by two types of natural aldolases: water-compatible organocatalysts and Zn(II) complexes. AU - Paradowska,Joanna, AU - Pasternak,Monika, AU - Gut,Bartosz, AU - Gryzło,Beata, AU - Mlynarski,Jacek, Y1 - 2011/12/19/ PY - 2011/12/6/entrez PY - 2011/12/6/pubmed PY - 2012/6/8/medline SP - 173 EP - 87 JF - The Journal of organic chemistry JO - J Org Chem VL - 77 IS - 1 N2 - In this article the utility of water-compatible amino-acid-based catalysts was explored in the development of diastereo- and enantioselective direct aldol reactions of a broad range of substrates. Chiral C(2)-symmetrical proline- and valine-based amides and their Zn(II) complexes were designed for use as efficient and flexible chiral catalysts for enantioselective aldol reactions in water, on water, and in the presence of water. The presence of 5 mol % of the prolinamide-based catalyst affords asymmetric intermolecular aldol reactions between unmodified ketones and various aldehydes to give anti products with excellent enantioselectivities. We also demonstrate aldol reactions of more demanding substrates with high affinity to water (i.e., acetone and formaldehyde). Newly designed serine-based organocatalyst promoted aldol reaction of hydroxyacetone leading to syn-diols. For presented catalytic systems organic solvent-free conditions are also acceptable, making the elaborated methodology interesting from a green chemistry perspectives. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/22136201/Direct_asymmetric_aldol_reactions_inspired_by_two_types_of_natural_aldolases:_water_compatible_organocatalysts_and_Zn_II__complexes_ L2 - https://doi.org/10.1021/jo201584w DB - PRIME DP - Unbound Medicine ER -