TY - JOUR A1 - Isoda, Motoyuki A1 - Sato, Kazuyuki A1 - Kunugi, Yurika A1 - Tokonishi, Satsuki A1 - Tarui, Atsushi A1 - Omote, Masaaki A1 - Minami, Hideki A1 - Ando, Akira T1 - Rh-Catalyzed reductive Mannich-type reaction and its application towards the synthesis of (±)-ezetimibe JF - Beilstein Journal of Organic Chemistry PY - 2016/// VL - 12 SP - 1608 EP - 1615 SN - 1860-5397 DO - 10.3762/bjoc.12.157 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.12.157 KW - β-lactam KW - ezetimibe KW - reductive Mannich-type reaction KW - rhodium–hydride KW - zinc enolate N2 - 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. ER -