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Issue 6, 2013
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A new and more powerfully activating diamine for practical and scalable enantioselective aldehyde crotylsilylation reactions

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Abstract

A new diaminophenol ligand for crotylsilylation reactions with cis- and trans-crotyltrichlorosilane has been developed. The conformational constraints that result from the tethering of the phenol to one of the amino groups attenuate the stereoelectronic effects that reduce activity in the corresponding untethered diaminosilanes, and the resulting crotylsilane reagents are as active as our previously reported EZ-CrotylMix reagents, but without requiring the use of the Sc(OTf)3 catalyst. In turn, this has allowed the development of an experimentally straightforward, sustainable, efficient, and scalable one-pot procedure which may be carried out in ≤8 hours, and in which the diaminophenol activator ligand may be easily recovered in ≥90% yield by recrystallization.

Graphical abstract: A new and more powerfully activating diamine for practical and scalable enantioselective aldehyde crotylsilylation reactions

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Publication details

The article was received on 14 Mar 2013, accepted on 09 Apr 2013 and first published on 09 Apr 2013


Article type: Edge Article
DOI: 10.1039/C3SC50714A
Citation: Chem. Sci., 2013,4, 2413-2417
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    A new and more powerfully activating diamine for practical and scalable enantioselective aldehyde crotylsilylation reactions

    L. M. Suen, M. L. Steigerwald and J. L. Leighton, Chem. Sci., 2013, 4, 2413
    DOI: 10.1039/C3SC50714A

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