高等学校化学学报2011，Vol.32Issue(10)：2331-2334,4.
(S,S)-TsDPEN-Ru催化不对称氢转移还原β-胺基酮及在度洛西汀合成中的应用
Asymmetric Transfer Hydrogenation ofβ-Amino Ketone Catalyzed by (S,S)-TsDPEN-Ru Complex and Its Application in the Synthesis of Duloxetine
摘要
Abstract
S) -γ-aminoalcohol is a key intermediate for the preparation of Duloxetine. In this paper, we describe an effective method to obtain ( S) -γ-aminoalcohol through asymmetric transfer hydrogenation with an easy accessible (S,S)-TsDPEN-Ru complex as catalyst in HCOOH/Et3N system. A variety of β-amino ke-tones were examined. Β-Amino ketones with donating groups (3a-3c) decomposed to give 1-(2-thienyl)-1-propanone during the reaction. On the other hand, (S)-γ-aminoalcohols with withdrawing groups(4e, 4f) were obtained in high e. E. Values( >95% ) and good yields under the optimal reaction conditions. This novel procedure was applied in the asymmetric total synthesis of duloxetine as a key step. Starting from acetyl thio-phene, duloxetine was obtained in a yield of 69% and e. E. Value of 91. 7%.关键词
度洛西汀/不对称氢转移/(S,S) -TsDPEN-Ru络合物Key words
uloxetine/ Asymmetric transfer hydrogenation/ (S,S)-TsDPEN-Ru complex分类
化学化工引用本文复制引用
赵金凤,窦海建,周宇涵,曲景平..(S,S)-TsDPEN-Ru催化不对称氢转移还原β-胺基酮及在度洛西汀合成中的应用[J].高等学校化学学报,2011,32(10):2331-2334,4.基金项目
国家自然科学基金(批准号:20572011)和大连市留学回国人员科研基金(批准号:2005J22JH021)资助. （批准号:20572011）
