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Study of the lanthanide-catalyzed, aqueous, asymmetric Mukaiyama aldol reaction.
J Org Chem. 2012 Jul 06; 77(13):5624-32.JO

Abstract

The development of efficient methods for the asymmetric Mukaiyama aldol reaction in aqueous solution has received great attention. We have developed a new series of chiral lanthanide-containing complexes that produce Mukaiyama aldol products with outstanding enantioselectivities. In this paper, we describe an optimized ligand synthesis, trends in stereoselectivity that result from changing lanthanide ions, and an exploration of substrate scope that includes aromatic and aliphatic aldehydes and silyl enol ethers derived from aromatic and aliphatic ketones.

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Publisher Full Text (DOI)

Authors+Show Affiliations

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

MeSH

AldehydesCatalysisLanthanoid Series ElementsMolecular StructureOrganometallic CompoundsStereoisomerismWater

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

22697304

Citation

Mei, Yujiang, et al. "Study of the Lanthanide-catalyzed, Aqueous, Asymmetric Mukaiyama Aldol Reaction." The Journal of Organic Chemistry, vol. 77, no. 13, 2012, pp. 5624-32.
Mei Y, Averill DJ, Allen MJ. Study of the lanthanide-catalyzed, aqueous, asymmetric Mukaiyama aldol reaction. J Org Chem. 2012;77(13):5624-32.
Mei, Y., Averill, D. J., & Allen, M. J. (2012). Study of the lanthanide-catalyzed, aqueous, asymmetric Mukaiyama aldol reaction. The Journal of Organic Chemistry, 77(13), 5624-32. https://doi.org/10.1021/jo300800b
Mei Y, Averill DJ, Allen MJ. Study of the Lanthanide-catalyzed, Aqueous, Asymmetric Mukaiyama Aldol Reaction. J Org Chem. 2012 Jul 6;77(13):5624-32. PubMed PMID: 22697304.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Study of the lanthanide-catalyzed, aqueous, asymmetric Mukaiyama aldol reaction. AU - Mei,Yujiang, AU - Averill,Derek J, AU - Allen,Matthew J, Y1 - 2012/06/14/ PY - 2012/6/16/entrez PY - 2012/6/16/pubmed PY - 2012/11/6/medline SP - 5624 EP - 32 JF - The Journal of organic chemistry JO - J Org Chem VL - 77 IS - 13 N2 - The development of efficient methods for the asymmetric Mukaiyama aldol reaction in aqueous solution has received great attention. We have developed a new series of chiral lanthanide-containing complexes that produce Mukaiyama aldol products with outstanding enantioselectivities. In this paper, we describe an optimized ligand synthesis, trends in stereoselectivity that result from changing lanthanide ions, and an exploration of substrate scope that includes aromatic and aliphatic aldehydes and silyl enol ethers derived from aromatic and aliphatic ketones. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/22697304/Study_of_the_lanthanide_catalyzed_aqueous_asymmetric_Mukaiyama_aldol_reaction_ L2 - https://doi.org/10.1021/jo300800b DB - PRIME DP - Unbound Medicine ER -