Journal
TETRAHEDRON
Volume 67, Issue 35, Pages 6539-6546Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.05.109
Keywords
Asymmetric-catalysis; Aldol reaction; Thioamide; Atorvastatin; Mesitylcopper
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Funding
- Sumitomo Foundation
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A new catalytic system was developed for the direct catalytic asymmetric aldol reaction of thioamides. The new lithium-free Cu catalyst (second-generation catalyst) exhibited enhanced catalytic efficiency over the previously developed catalyst comprising [Cu(CH(3)CN)(4)]PF(6)/Ph-BPE/LiOAr (first-generation catalyst), which required a tedious catalyst preparation process. In the reaction with the second-generation catalyst, the intermediate Cu-aldolate functioned as a Bronsted base to generate thioamide enolate, efficiently driving the catalytic cycle. The present aldol methodology culminated ill a concise asymmetric synthesis of atorvastatin (Lipitor (R): atorvastatin calcium), a widely prescribed HMG-CoA reductase inhibitor for lowering low-density lipoprotein cholesterol. (C) 2011 Elsevier Ltd. All rights reserved.
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