Asymmetric Michael Additions of α-Nitrocyclohexanone to Aryl Nitroalkenes Catalyzed by Natural Amino Acid-Derived Bifunctional Thioureas
✍ Scribed by Jörres, Manuel; Schiffers, Ingo; Atodiresei, Iuliana; Bolm, Carsten
- Book ID
- 120287890
- Publisher
- American Chemical Society
- Year
- 2012
- Tongue
- English
- Weight
- 358 KB
- Volume
- 14
- Category
- Article
- ISSN
- 1523-7060
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📜 SIMILAR VOLUMES
## Abstract An easy and simple synthetic approach to optically active α,α‐quaternary α‐amino acids using asymmetric organocatalysis is presented. The addition of oxazolones to nitroalkenes catalyzed by thiourea cinchona derivatives provides the corresponding α,α‐quaternary α‐amino acid derivatives
A series of secondary amine-thiourea catalysts derived from L-proline and chiral diamine were prepared and first applied to the Michael addition of a,a-disubstituted aldehydes to trans-b-nitroalkenes. Moderate yields (47-75%) and excellent enantioselectivities (up to 96% ee) were obtained for a vari