Non-linear effects operate and dynamic ligand exchange occurs when chiral BINOL-boron Lewis acids are used for asymmetric catalysis

J P Cros, Y Perez-Fuertes, M J Thatcher, S Arimori, S D Bull, T D James

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Non-linear effects reveal that the use of chiral BINOL-boron reagents for aza-Diels-Alder reactions results in an enantioselective catalytic species containing at least 2 equiv. of BINOL. Dynamic ligand exchange and ligand accelerated catalysis occurs in these reactions, consistent with the formation of a cyclic borate ester of BINOL with enhanced Lewis acidity. (C) 2003 Elsevier Science Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)1965-1968
Number of pages4
JournalTetrahedron: Asymmetry
Volume14
Issue number14
DOIs
Publication statusPublished - 2003

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Lewis Acids
Boron
Catalysis
catalysis
boron
Ligands
Diels-Alder reactions
ligands
acids
Acids
borates
Acidity
acidity
reagents
esters
Ion exchange
Esters
Borates
naphthol BINOL

Cite this

Non-linear effects operate and dynamic ligand exchange occurs when chiral BINOL-boron Lewis acids are used for asymmetric catalysis. / Cros, J P; Perez-Fuertes, Y; Thatcher, M J; Arimori, S; Bull, S D; James, T D.

In: Tetrahedron: Asymmetry, Vol. 14, No. 14, 2003, p. 1965-1968.

Research output: Contribution to journalArticle

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AU - Bull, S D

AU - James, T D

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AB - Non-linear effects reveal that the use of chiral BINOL-boron reagents for aza-Diels-Alder reactions results in an enantioselective catalytic species containing at least 2 equiv. of BINOL. Dynamic ligand exchange and ligand accelerated catalysis occurs in these reactions, consistent with the formation of a cyclic borate ester of BINOL with enhanced Lewis acidity. (C) 2003 Elsevier Science Ltd. All rights reserved.

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