Enantioselective catalysis of the Henry reaction by a chiral macrocyclic ytterbium complex in aqueous media

Shashi U. Pandya; Rachel S. Dickins; David Parker

doi:10.1039/b712470h

Enantioselective catalysis of the Henry reaction by a chiral macrocyclic ytterbium complex in aqueous media

Shashi U. Pandya, Rachel S. Dickins, David Parker^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

18 Citations (Scopus)

Abstract

A chiral macrocyclic ytterbium cationic complex catalyses the nitro-aldol reaction between α-ketocarboxylates and nitromethane under ambient aqueous conditions, leading to the formation of for example, methyl-2-hydroxy-2-methyl- 3-nitropropanoate in 96% yield and 59% enantiomeric purity. Monitoring of the paramagnetically shifted intermediate Yb species by ¹H NMR allows several different species on the catalytic cycle to be identified and is consistent with the intermediacy of stereoisomeric chelated pyruvates of differing reactivity towards the nucleophile, as well as product inhibition of turnover.

Original language	English
Pages (from-to)	3842-3846
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	5
Issue number	23
DOIs	https://doi.org/10.1039/b712470h
Publication status	Published - 29 Oct 2007

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title = "Enantioselective catalysis of the Henry reaction by a chiral macrocyclic ytterbium complex in aqueous media",

abstract = "A chiral macrocyclic ytterbium cationic complex catalyses the nitro-aldol reaction between α-ketocarboxylates and nitromethane under ambient aqueous conditions, leading to the formation of for example, methyl-2-hydroxy-2-methyl- 3-nitropropanoate in 96% yield and 59% enantiomeric purity. Monitoring of the paramagnetically shifted intermediate Yb species by 1H NMR allows several different species on the catalytic cycle to be identified and is consistent with the intermediacy of stereoisomeric chelated pyruvates of differing reactivity towards the nucleophile, as well as product inhibition of turnover.",

author = "Pandya, {Shashi U.} and Dickins, {Rachel S.} and David Parker",

note = "We thank the EPSRC for support, and Dr Pierre-Yves Chavant for fruitful discussions. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2007",

year = "2007",

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doi = "10.1039/b712470h",

language = "English",

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T1 - Enantioselective catalysis of the Henry reaction by a chiral macrocyclic ytterbium complex in aqueous media

AU - Pandya, Shashi U.

AU - Dickins, Rachel S.

AU - Parker, David

N1 - We thank the EPSRC for support, and Dr Pierre-Yves Chavant for fruitful discussions. Publisher Copyright: © The Royal Society of Chemistry 2007

PY - 2007/10/29

Y1 - 2007/10/29

N2 - A chiral macrocyclic ytterbium cationic complex catalyses the nitro-aldol reaction between α-ketocarboxylates and nitromethane under ambient aqueous conditions, leading to the formation of for example, methyl-2-hydroxy-2-methyl- 3-nitropropanoate in 96% yield and 59% enantiomeric purity. Monitoring of the paramagnetically shifted intermediate Yb species by 1H NMR allows several different species on the catalytic cycle to be identified and is consistent with the intermediacy of stereoisomeric chelated pyruvates of differing reactivity towards the nucleophile, as well as product inhibition of turnover.

AB - A chiral macrocyclic ytterbium cationic complex catalyses the nitro-aldol reaction between α-ketocarboxylates and nitromethane under ambient aqueous conditions, leading to the formation of for example, methyl-2-hydroxy-2-methyl- 3-nitropropanoate in 96% yield and 59% enantiomeric purity. Monitoring of the paramagnetically shifted intermediate Yb species by 1H NMR allows several different species on the catalytic cycle to be identified and is consistent with the intermediacy of stereoisomeric chelated pyruvates of differing reactivity towards the nucleophile, as well as product inhibition of turnover.

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UR - https://pubs.rsc.org/en/content/articlelanding/2007/ob/b712470h

U2 - 10.1039/b712470h

DO - 10.1039/b712470h

M3 - Journal article

AN - SCOPUS:36148967632

SN - 1477-0520

VL - 5

SP - 3842

EP - 3846

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 23

ER -

Enantioselective catalysis of the Henry reaction by a chiral macrocyclic ytterbium complex in aqueous media

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