Chiral lactones and lactams are endowed with a large spectrum of biological properties [1] including very important pharmaceutical activities. [2] The chiral piperidines (À)paroxetine hydrochloride 1, marketed as paxil/seroxat, and (+)-femoxetine 2 are selective serotonin reuptake inhibitors and are
Organocatalytic Conjugate Addition of Malonates to α,β-Unsaturated Aldehydes: Asymmetric Formal Synthesis of (−)-Paroxetine, Chiral Lactams, and Lactones
✍ Scribed by Sven Brandau; Aitor Landa; Johan Franzén; Mauro Marigo; Karl Anker Jørgensen
- Publisher
- John Wiley and Sons
- Year
- 2006
- Tongue
- English
- Weight
- 167 KB
- Volume
- 118
- Category
- Article
- ISSN
- 0044-8249
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📜 SIMILAR VOLUMES
## Abstract The first example of an organocatalytic asymmetric Michael addition of aldehydes to α,β‐unsaturated thiol esters promoted by chiral diphenylprolinol silyl ether is presented. The reaction occurs with good yields, diastereoselectivity and excellent enantioselectivity.
Organocatalysis [1] has expanded widely within the last few years, since the rediscovery of the proline-catalyzed aldol reaction. [2] Since then, several different methods, such as fluorination, [3] chlorination, [4] bromination, [5] sulfenylation, [6] amination, [7] and Mannich reactions, [8] have