A new Yb3+-catalyzed pinacol and imine-coupling reaction

Helen C. Aspinall; Nicholas Greeves; Shane Lo Fan Hin

doi:10.1016/j.tetlet.2010.01.057

A new Yb³⁺-catalyzed pinacol and imine-coupling reaction

Helen C. Aspinall^*, Nicholas Greeves, Shane Lo Fan Hin

^*Corresponding author for this work

University of Liverpool

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

Abstract

Ytterbium triflate, Yb(OTf)₃, catalyzes the intermolecular reductive homocouplings of imines, aldehydes, and ketones at loadings of 5 mol % in the presence of Mg and Me₃SiCl to give isolated yields of up to 95%. Diastereoselectivity of up to 4/96 (dl/meso) is achieved for aromatic aldehydes, up to 100% dl for aliphatic aldehydes, and 100% dl for an intramolecular imine coupling.

Original language	English
Pages (from-to)	1558-1561
Number of pages	4
Journal	Tetrahedron Letters
Volume	51
Issue number	12
DOIs	https://doi.org/10.1016/j.tetlet.2010.01.057
Publication status	Published - 24 Mar 2010
Externally published	Yes

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title = "A new Yb3+-catalyzed pinacol and imine-coupling reaction",

abstract = "Ytterbium triflate, Yb(OTf)3, catalyzes the intermolecular reductive homocouplings of imines, aldehydes, and ketones at loadings of 5 mol % in the presence of Mg and Me3SiCl to give isolated yields of up to 95%. Diastereoselectivity of up to 4/96 (dl/meso) is achieved for aromatic aldehydes, up to 100% dl for aliphatic aldehydes, and 100% dl for an intramolecular imine coupling.",

author = "Aspinall, {Helen C.} and Nicholas Greeves and Hin, {Shane Lo Fan}",

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AU - Aspinall, Helen C.

AU - Greeves, Nicholas

AU - Hin, Shane Lo Fan

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N2 - Ytterbium triflate, Yb(OTf)3, catalyzes the intermolecular reductive homocouplings of imines, aldehydes, and ketones at loadings of 5 mol % in the presence of Mg and Me3SiCl to give isolated yields of up to 95%. Diastereoselectivity of up to 4/96 (dl/meso) is achieved for aromatic aldehydes, up to 100% dl for aliphatic aldehydes, and 100% dl for an intramolecular imine coupling.

AB - Ytterbium triflate, Yb(OTf)3, catalyzes the intermolecular reductive homocouplings of imines, aldehydes, and ketones at loadings of 5 mol % in the presence of Mg and Me3SiCl to give isolated yields of up to 95%. Diastereoselectivity of up to 4/96 (dl/meso) is achieved for aromatic aldehydes, up to 100% dl for aliphatic aldehydes, and 100% dl for an intramolecular imine coupling.

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SP - 1558

EP - 1561

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 12

ER -

A new Yb³⁺-catalyzed pinacol and imine-coupling reaction

Abstract

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