Abstract
N-Alkenyl ureas and N-alkenyl carbamates, like other N-acyl enamines, are typically nucleophilic at their β-carbon. However, by incorporating an α-aryl substituent, we show that they will also undergo attack at the β-carbon by organolithium nucleophiles, leading to the products of carbolithiation. The carbolithiation of E and Z N-alkenyl ureas is diastereospecific, and N-tert-butoxy-carbonyl N-alkenyl carbamates give carbolithiation products that may be deprotected in situ to provide a new connective route to hindered amines. © 2013 Lefranc et al.
| Original language | English |
|---|---|
| Pages (from-to) | 628-632 |
| Number of pages | 4 |
| Journal | Beilstein Journal of Organic Chemistry |
| Volume | 9 |
| DOIs | |
| Publication status | Published - 28 Mar 2013 |
Keywords
- Carbamate
- Carbolithiation
- Carbometallation
- Organolithium
- Stereospecificity
- Styrene
- Urea
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CCDC 919578: Experimental Crystal Structure Determination
Lefranc, J. (Contributor), Minassi, A. (Contributor) & Clayden, J. (Contributor), Cambridge Crystallographic Data Centre, 2013
DOI: 10.5517/cczvwth, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cczvwth&sid=DataCite
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CCDC 919577: Experimental Crystal Structure Determination
Lefranc, J. (Contributor), Minassi, A. (Contributor) & Clayden, J. (Contributor), Cambridge Crystallographic Data Centre, 2013
DOI: 10.5517/cczvwsg, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cczvwsg&sid=DataCite
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