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Nat Chem. 2011 Dec 4;4(1):45-51. doi: 10.1038/nchem.1212.

Three-component reaction discovery enabled by mass spectrometry of self-assembled monolayers.

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1
Chicago Tri-Institutional Center for Chemical Methods and Library Development, Department of Chemistry, University of Chicago, Chicago, Illinois 60637, USA.

Abstract

Multicomponent reactions are employed extensively in many areas of organic chemistry. Despite significant progress, the discovery of such enabling transformations remains challenging. Here, we present the development of a parallel, label-free reaction-discovery platform that can be used in the identification of new multicomponent transformations. Our approach is based on parallel mass spectrometric screening of interfacial chemical reactions on arrays of self-assembled monolayers. This strategy enabled the identification of a simple organic phosphine that can catalyse a previously unknown condensation of siloxyalkynes, aldehydes and amines to produce 3-hydroxyamides with high efficiency and diastereoselectivity. The reaction was further optimized using solution-phase methods.

PMID:
22169871
PMCID:
PMC3243075
DOI:
10.1038/nchem.1212
[Indexed for MEDLINE]
Free PMC Article

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