title: Rh-Catalyzed reductive Mannich-type reaction and its application towards the synthesis of (±)-ezetimibe.
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.
authors: Faculty of Pharmaceutical Sciences, Setsunan University 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan.
authors: Motoyuki
authors: M
authors: Isoda
authors: Faculty of Pharmaceutical Sciences, Setsunan University 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan.
authors: Kazuyuki
authors: K
authors: Sato
authors: Faculty of Pharmaceutical Sciences, Setsunan University 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan.
authors: Yurika
authors: Y
authors: Kunugi
authors: Faculty of Pharmaceutical Sciences, Setsunan University 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan.
authors: Satsuki
authors: S
authors: Tokonishi
authors: Faculty of Pharmaceutical Sciences, Setsunan University 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan.
authors: Atsushi
authors: A
authors: Tarui
authors: Faculty of Pharmaceutical Sciences, Setsunan University 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan.
authors: Masaaki
authors: M
authors: Omote
authors: Faculty of Pharmaceutical Sciences, Hiroshima International University, 5-1-1 Hirokoshingai, Kure, Hiroshima 737-0112, Japan.
authors: Hideki
authors: H
authors: Minami
authors: Faculty of Pharmaceutical Sciences, Setsunan University 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan.
authors: Akira
authors: A
authors: Ando
keywords: ezetimibe; reductive Mannich-type reaction; rhodium–hydride; zinc enolate; β-lactam