铑催化的还原曼尼希型反应及其在（±）-依泽替米贝合成中的应用。
Rh-Catalyzed reductive Mannich-type reaction and its application towards the synthesis of (±)-ezetimibe.
作者信息
Isoda Motoyuki, Sato Kazuyuki, Kunugi Yurika, Tokonishi Satsuki, Tarui Atsushi, Omote Masaaki, Minami Hideki, Ando Akira
机构信息
Faculty of Pharmaceutical Sciences, Setsunan University 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan.
Faculty of Pharmaceutical Sciences, Hiroshima International University, 5-1-1 Hirokoshingai, Kure, Hiroshima 737-0112, Japan.
出版信息
Beilstein J Org Chem. 2016 Jul 27;12:1608-15. doi: 10.3762/bjoc.12.157. eCollection 2016.
Abstract
An effective synthesis for syn-β-lactams was achieved using a Rh-catalyzed reductive Mannich-type reaction. A rhodium-hydride complex (Rh-H) derived from diethylzinc (Et2Zn) and a Rh catalyst was used for the 1,4-reduction of an α,β-unsaturated ester to give a Reformatsky-type reagent, which in turn, reacted with an imine to give the syn-β-lactam. Additionally, the reaction was applied to the synthesis of (±)-ezetimibe, a potent β-lactamic cholesterol absorption inhibitor.
摘要
通过铑催化的还原曼尼希型反应实现了对顺式β-内酰胺的有效合成。由二乙基锌（Et2Zn）和铑催化剂衍生得到的氢化铑配合物（Rh-H）用于α,β-不饱和酯的1,4-还原反应，生成一种类雷福尔马茨基试剂，该试剂进而与亚胺反应生成顺式β-内酰胺。此外，该反应还应用于合成强效β-内酰胺类胆固醇吸收抑制剂（±）-依泽替米贝。
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