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.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 45-51 |
| Number of pages | 7 |
| Journal | Nature chemistry |
| Volume | 4 |
| Issue number | 1 |
| DOIs | |
| State | Published - Jan 2012 |
Funding
This work was funded by the National Institutes of Health (P50 GM086145) and the Chicago Biomedical Consortium with support from the Searle Funds at the Chicago Community Trust. We thank Ian Steele for the X-ray crystallographic analysis of 5.
ASJC Scopus subject areas
- General Chemical Engineering
- General Chemistry