A site isolation-enabled organocatalytic approach to enantiopure γ-amino alcohol drugs. Issue 29 (19th July 2018)

• Record Type: Journal Article
• Authors: Wang, Shoulei; Rodríguez-Escrich, Carles; Fan, Xinyuan; Pericàs, Miquel A.
• Is Part Of: Tetrahedron. Volume 74:Issue 29(2018)
• Page Start: 3943
• Page End: 3946
• Publication Date: 2018-07-19
• Subjects: Solid-supported catalysts -- Site isolation -- η6-Arene chromium complexes -- γ-Amino alcohol drugs -- Phenoperidine; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.04.022
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Solid support-enabled site isolation has previously allowed to use paraldehyde as an acetaldehyde surrogate in aldol reactions. However, only electron-poor aldehydes were tolerated by the system. Herein, we show that the temporary conversion of benzaldehyde into η 6 -benzaldehyde Cr(CO)3 circumvents this limitation. Asymmetric synthesis of ( R )-Phenoperidine, as well as formal syntheses of ( R )-Fluoxetine and ( R )-Atomoxetine, illustrate the benefits of this strategy. Graphical abstract: Image 1