Rh-Catalyzed reductive Mannich-type reaction and its application towards the synthesis of (±)-ezetimibe

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 (Et(2)Zn) 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 tu...

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Autores principales: Isoda, Motoyuki, Sato, Kazuyuki, Kunugi, Yurika, Tokonishi, Satsuki, Tarui, Atsushi, Omote, Masaaki, Minami, Hideki, Ando, Akira
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4979637/
https://www.ncbi.nlm.nih.gov/pubmed/27559413
http://dx.doi.org/10.3762/bjoc.12.157
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author Isoda, Motoyuki
Sato, Kazuyuki
Kunugi, Yurika
Tokonishi, Satsuki
Tarui, Atsushi
Omote, Masaaki
Minami, Hideki
Ando, Akira
author_facet Isoda, Motoyuki
Sato, Kazuyuki
Kunugi, Yurika
Tokonishi, Satsuki
Tarui, Atsushi
Omote, Masaaki
Minami, Hideki
Ando, Akira
author_sort Isoda, Motoyuki
collection PubMed
description 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 (Et(2)Zn) 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.
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spelling pubmed-49796372016-08-24 Rh-Catalyzed reductive Mannich-type reaction and its application towards the synthesis of (±)-ezetimibe Isoda, Motoyuki Sato, Kazuyuki Kunugi, Yurika Tokonishi, Satsuki Tarui, Atsushi Omote, Masaaki Minami, Hideki Ando, Akira Beilstein J Org Chem Full Research Paper 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 (Et(2)Zn) 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. Beilstein-Institut 2016-07-27 /pmc/articles/PMC4979637/ /pubmed/27559413 http://dx.doi.org/10.3762/bjoc.12.157 Text en Copyright © 2016, Isoda et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Isoda, Motoyuki
Sato, Kazuyuki
Kunugi, Yurika
Tokonishi, Satsuki
Tarui, Atsushi
Omote, Masaaki
Minami, Hideki
Ando, Akira
Rh-Catalyzed reductive Mannich-type reaction and its application towards the synthesis of (±)-ezetimibe
title Rh-Catalyzed reductive Mannich-type reaction and its application towards the synthesis of (±)-ezetimibe
title_full Rh-Catalyzed reductive Mannich-type reaction and its application towards the synthesis of (±)-ezetimibe
title_fullStr Rh-Catalyzed reductive Mannich-type reaction and its application towards the synthesis of (±)-ezetimibe
title_full_unstemmed Rh-Catalyzed reductive Mannich-type reaction and its application towards the synthesis of (±)-ezetimibe
title_short Rh-Catalyzed reductive Mannich-type reaction and its application towards the synthesis of (±)-ezetimibe
title_sort rh-catalyzed reductive mannich-type reaction and its application towards the synthesis of (±)-ezetimibe
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4979637/
https://www.ncbi.nlm.nih.gov/pubmed/27559413
http://dx.doi.org/10.3762/bjoc.12.157
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