(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 |
| |
| Authors: | Yuichiro Ashida Yuka Sato Takeyuki Suzuki Kanako Ueno Ken‐ichiro Kai Dr Hidefumi Nakatsuji Prof Dr Yoo Tanabe |
| |
| Affiliation: | 1. Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2‐1 Gakuen, Sanda, Hyogo 669‐1337 (Japan);2. Graduate School of Engineering, Nagoya University Furo‐cho, Chikusa, Nagoya 464‐8603 (Japan) |
| |
| Abstract: | Parallel and practical methods for the preparation of both (E)‐ and (Z)‐β‐aryl1‐β‐aryl2‐α,β‐unsaturated esters 1 and (E)‐ and (Z)‐α‐aryl1‐β‐aryl2‐α,β‐unsaturated esters 2 are described. These methods involve accessible, robust, stereocomplementary N‐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 (E)‐ and (Z)‐pure products 1 and 2 by utilizing sequential enol tosylations and cross‐coupling reactions. An expeditious and parallel synthesis of (E)‐ and (Z)‐zimelidine ( 3 ), which is a highly representative selective serotonin reuptake inhibitor (SSRI), was performed by utilizing the present methods. |
| |
| Keywords: | cross‐coupling esters enols parallel synthesis synthesis design |
|
|
