Enantioselective Synthesis of a Highly Potent Selective Serotonin Reuptake Inhibitor. An Application of Imidazolidinone Catalysis to the Alkylation of Indoles with an α,β-Disubstituted α,β-Unsaturated Aldehyde
Organic Letters2005Vol. 7(16), pp. 3437–3440
Citations Over TimeTop 10% of 2005 papers
Dalton King, Zhaoxing Meng, Derek J. Denhart, Ronald J. Mattson, Roy Kimura, Dedong Wu, Qi Gao, John E. Macor
Abstract
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]
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