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Direct asymmetric aldol reactions between aldehydes and ketones catalyzed by L-tryptophan in the presence of water.
Org Biomol Chem. 2010 Mar 21; 8(6):1368-77.OB

Abstract

Primary amino acids and their derivatives were investigated as catalysts for the direct asymmetric aldol reactions between ketones and aldehydes in the presence of water, and L-tryptophan was shown to be the best catalyst. Solvent effects, substrate scope and the influence of water on the reactions were investigated. Quantum chemical calculations were performed to understand the origin of the observed stereoselectivity.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Jiang Z
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543, Republic of Singapore.
Yang H
No affiliation info available
Han X
No affiliation info available
Luo J
No affiliation info available
Wong MW
No affiliation info available
Lu Y
No affiliation info available

MeSH

AldehydesCatalysisKetonesModels, MolecularMolecular ConformationQuantum TheorySolventsStereoisomerismSubstrate SpecificityTryptophanWater

Pub Type(s)

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

Language

eng

PubMed ID

20204209

Citation

Jiang, Zhaoqin, et al. "Direct Asymmetric Aldol Reactions Between Aldehydes and Ketones Catalyzed By L-tryptophan in the Presence of Water." Organic & Biomolecular Chemistry, vol. 8, no. 6, 2010, pp. 1368-77.
Jiang Z, Yang H, Han X, et al. Direct asymmetric aldol reactions between aldehydes and ketones catalyzed by L-tryptophan in the presence of water. Org Biomol Chem. 2010;8(6):1368-77.
Jiang, Z., Yang, H., Han, X., Luo, J., Wong, M. W., & Lu, Y. (2010). Direct asymmetric aldol reactions between aldehydes and ketones catalyzed by L-tryptophan in the presence of water. Organic & Biomolecular Chemistry, 8(6), 1368-77. https://doi.org/10.1039/b921460g
Jiang Z, et al. Direct Asymmetric Aldol Reactions Between Aldehydes and Ketones Catalyzed By L-tryptophan in the Presence of Water. Org Biomol Chem. 2010 Mar 21;8(6):1368-77. PubMed PMID: 20204209.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Direct asymmetric aldol reactions between aldehydes and ketones catalyzed by L-tryptophan in the presence of water. AU - Jiang,Zhaoqin, AU - Yang,Hui, AU - Han,Xiao, AU - Luo,Jie, AU - Wong,Ming Wah, AU - Lu,Yixin, Y1 - 2010/01/22/ PY - 2010/3/6/entrez PY - 2010/3/6/pubmed PY - 2010/6/10/medline SP - 1368 EP - 77 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 8 IS - 6 N2 - Primary amino acids and their derivatives were investigated as catalysts for the direct asymmetric aldol reactions between ketones and aldehydes in the presence of water, and L-tryptophan was shown to be the best catalyst. Solvent effects, substrate scope and the influence of water on the reactions were investigated. Quantum chemical calculations were performed to understand the origin of the observed stereoselectivity. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/20204209/Direct_asymmetric_aldol_reactions_between_aldehydes_and_ketones_catalyzed_by_L_tryptophan_in_the_presence_of_water_ L2 - https://doi.org/10.1039/b921460g DB - PRIME DP - Unbound Medicine ER -