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A new class of ligands for aqueous, lanthanide-catalyzed, enantioselective Mukaiyama aldol reactions.
J Am Chem Soc. 2010 Sep 22; 132(37):12871-3.JA

Abstract

The development of aqueous methods for generating enantiopure β-hydroxy carbonyl compounds is an important goal because these subunits compose many bioactive compounds and the ability to synthesize these groups in water has environmental and cost benefits. In this communication, we report a new class of ligands for aqueous, lanthanide-catalyzed, asymmetric Mukaiyama aldol reactions for the synthesis of chiral β-hydroxy ketones. Furthermore, we have used luminescence-decay measurements to unveil mechanistic information regarding the catalytic reaction via changes in water-coordination number. The precatalysts presented here yielded β-hydroxy carbonyls from aliphatic and aryl substrates with outstanding syn:anti ratios and enantiometric excesses of up to 49:1 and 97%, respectively.

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Authors+Show Affiliations

Mei Y
Department of Chemistry, Wayne State University, Detroit, Michigan 48202, USA.
Dissanayake P
No affiliation info available
Allen MJ
No affiliation info available

MeSH

AldehydesCatalysisLanthanoid Series ElementsLigandsOrganometallic CompoundsStereoisomerismStructure-Activity RelationshipSubstrate SpecificityWater

Pub Type(s)

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

Language

eng

PubMed ID

20806902

Citation

Mei, Yujiang, et al. "A New Class of Ligands for Aqueous, Lanthanide-catalyzed, Enantioselective Mukaiyama Aldol Reactions." Journal of the American Chemical Society, vol. 132, no. 37, 2010, pp. 12871-3.
Mei Y, Dissanayake P, Allen MJ. A new class of ligands for aqueous, lanthanide-catalyzed, enantioselective Mukaiyama aldol reactions. J Am Chem Soc. 2010;132(37):12871-3.
Mei, Y., Dissanayake, P., & Allen, M. J. (2010). A new class of ligands for aqueous, lanthanide-catalyzed, enantioselective Mukaiyama aldol reactions. Journal of the American Chemical Society, 132(37), 12871-3. https://doi.org/10.1021/ja107197p
Mei Y, Dissanayake P, Allen MJ. A New Class of Ligands for Aqueous, Lanthanide-catalyzed, Enantioselective Mukaiyama Aldol Reactions. J Am Chem Soc. 2010 Sep 22;132(37):12871-3. PubMed PMID: 20806902.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A new class of ligands for aqueous, lanthanide-catalyzed, enantioselective Mukaiyama aldol reactions. AU - Mei,Yujiang, AU - Dissanayake,Prabani, AU - Allen,Matthew J, PY - 2010/9/3/entrez PY - 2010/9/3/pubmed PY - 2011/1/5/medline SP - 12871 EP - 3 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 132 IS - 37 N2 - The development of aqueous methods for generating enantiopure β-hydroxy carbonyl compounds is an important goal because these subunits compose many bioactive compounds and the ability to synthesize these groups in water has environmental and cost benefits. In this communication, we report a new class of ligands for aqueous, lanthanide-catalyzed, asymmetric Mukaiyama aldol reactions for the synthesis of chiral β-hydroxy ketones. Furthermore, we have used luminescence-decay measurements to unveil mechanistic information regarding the catalytic reaction via changes in water-coordination number. The precatalysts presented here yielded β-hydroxy carbonyls from aliphatic and aryl substrates with outstanding syn:anti ratios and enantiometric excesses of up to 49:1 and 97%, respectively. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/20806902/A_new_class_of_ligands_for_aqueous_lanthanide_catalyzed_enantioselective_Mukaiyama_aldol_reactions_ L2 - https://doi.org/10.1021/ja107197p DB - PRIME DP - Unbound Medicine ER -