(E)‐, (Z)‐Parallel Preparative Methods for Stereodefined β, β‐Diaryl‐ and α, β‐Diaryl‐α, β‐unsaturated Esters: Application to the Stereocomplementary Concise Synthesis of Zimelidine. Issue 15 (27th February 2015)

• Record Type: Journal Article
• Authors: Ashida, Yuichiro; Sato, Yuka; Suzuki, Takeyuki; Ueno, Kanako; Kai, Ken‐ichiro; Nakatsuji, Hidefumi; Tanabe, Yoo
• Is Part Of: Chemistry. Volume 21:Issue 15(2015)
• Page Start: 5934
• Page End: 5945
• Publication Date: 2015-02-27
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201405150
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Parallel and practical methods for the preparation of both (<italic>E</italic>)‐ and (<italic>Z</italic>)‐β‐aryl¹‐β‐aryl²‐α, β‐unsaturated esters <bold>1</bold> and (<italic>E</italic>)‐ and (<italic>Z</italic>)‐α‐aryl¹‐β‐aryl²‐α, β‐unsaturated esters <bold>2</bold> are described. These methods involve accessible, robust, stereocomplementary <italic>N</italic>‐methylimidazole (NMI)‐mediated enol tosylations (14 examples, 70–99 % yield), as well as stereoretentive Suzuki–Miyaura cross‐couplings (36 examples, 64–99 % yield). The highlighted feature of the present protocol is the use of parallel and stereocomplementary approaches to obtain highly (<italic>E</italic>)‐ and (<italic>Z</italic>)‐pure products <bold>1</bold> and <bold>2</bold> by utilizing sequential enol tosylations and cross‐coupling reactions. An expeditious and parallel synthesis of (<italic>E</italic>)‐ and (<italic>Z</italic>)‐zimelidine (<bold>3</bold>), which is a highly representative selective serotonin reuptake inhibitor (SSRI), was performed by utilizing the present methods.</p> </abstract>