Cover Picture: Stereocomplementary and Parallel Syntheses of Multi‐Substituted (E)‐, (Z)‐Stereodefined α, β‐Unsaturated Esters: Application to Drug Syntheses (Chem. Rec. 12/2020). Issue 12 (11th December 2020)

• Record Type: Journal Article
• Authors: Ashida, Yuichiro; Tanabe, Yoo
• Is Part Of: Chemical record. Volume 20:Issue 12(2020)
• Page Start: 1409
• Page End: 1409
• Publication Date: 2020-12-11
• Subjects: Cross-coupling -- Synthetic methods -- (E)- and (Z)-α, β-unsaturated esters -- Drug syntheses -- (E)- and (Z)-stereocomplementary and parallel synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/tcr.202081201
• Languages: English
• ISSNs: 1527-8999

Abstract

Abstract : The cover picture shows distinctive methodologies for stereo‐complementary syntheses of a variety of α, β‐unsaturated esters from highly accessible ( E )‐, ( Z )‐stereo‐defined enol tosylate cross‐coupling partners (Suzuki‐Miyaura, Negishi, Sonogashira, Iron‐catalyzed, Mizoroki‐Heck, Buchwald‐Hartwig reactions), derived from β‐ketoesters and α‐formyl esters. Notably, this strategy was successfully applied for parallel drug syntheses of ( E )‐ and ( Z )‐zimelidine, ( E )‐ and ( Z )‐tamoxifen, and Merck's cyclopropane pharmacophore. Representative successful utilizations by other groups are also introduced. See the Personal Account by Yuichiro Ashida and Yoo Tanabe (DOI: 10.1002/tcr.202000076 ).