Abstract
(Chemical Presented) It takes three : The stereoselective synthesis of highly substituted γ-lactams from amide enolates, acylsilanes, and imines is reported. This multicomponent reaction accesses γ-amino-β-hydroxy amides in a single flask with good yields and excellent levels of diastereoselectivity (see scheme). Exposure of the linear products to microwave irradiation and acidic conditions promotes a cyclization to form the corresponding γ-lactams in excellent yields.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 2294-2297 |
| Number of pages | 4 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 47 |
| Issue number | 12 |
| DOIs | |
| State | Published - Mar 7 2008 |
Keywords
- Acylsilanes
- Chiral auxiliaries
- Homoenolates
- Synthetic methods
- γ-lactams
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
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CCDC 676688: Experimental Crystal Structure Determination
Lettan II, R. B. (Contributor), Woodward, C. C. (Creator) & Scheidt, K. A. (Creator), Cambridge Crystallographic Data Centre, 2008
DOI: 10.5517/ccqq4n6, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccqq4n6&sid=DataCite
Dataset