Corpus ID: 21786013

Enantioselective synthesis of a highly potent selective serotonin reuptake inhibitor. An application of imidazolidinone catalysis to the alkylation of indoles with an alpha,beta-disubstituted alpha,beta-unsaturated aldehyde.

@article{King2005EnantioselectiveSO,
  title={Enantioselective synthesis of a highly potent selective serotonin reuptake inhibitor. An application of imidazolidinone catalysis to the alkylation of indoles with an alpha,beta-disubstituted alpha,beta-unsaturated aldehyde.},
  author={Hurley Dalton King and Zhaoxing Meng and Derek J. Denhart and Ronald J. Mattson and Roy Kimura and Dedong Wu and Qi Gao and John Eugene Macor},
  journal={Organic letters},
  year={2005},
  volume={7 16},
  pages={
          3437-40
        }
}
The synthesis of the highly potent and selective serotonin reuptake inhibitor 1 (BMS-594726) is described. In the key construction step, an enantioselective alkylation of the indole nucleus with an alpha-branched alpha,beta-unsaturated aldehyde 7 was accomplished utilizing MacMillan's imidazolidinone catalyst 3b. A rationale is presented for the unexpected stereochemical result, as well as the novel reactivity of the alpha-branched substrate. [reaction: see text]