An enamide‐based domino reaction for a highly stereoselective synthesis of tetrahydropyrans

A novel method for the highly stereoselective synthesis of tetrahydropyrans is reported. This domino reaction is based on a twofold addition of enamides to aldehydes followed by a subsequent cyclization and furnishes fully substituted tetrahydropyrans in high yields. Three new σ‐bonds and five continuous stereogenic centers are formed in this one‐pot process with a remarkable degree of diastereoselectivity. In most cases, the formation of only one out of 16 possible diastereomers is observed. Two different stereoisomers can be accessed in a controlled fashion starting either from an E‐ or a Z‐configured enamide.
Eine neuartige Dominoreaktion, basierend auf der zweifachen Addition von Enamiden an Aldehyde und einer nachfolgenden Cyclisierung, liefert fünffach substituierte Tetrahydropyrane in hohen Ausbeuten und hervorragenden Stereoselektivitäten. In einer einzigen Transformation werden dabei drei neue σ‐Bindungen und fünf fortlaufende Stereozentren aufgebaut. In den meisten Fällen wird eins von 16 möglichen Diastereomeren gebildet.

Metadaten
Author:	Philipp Kramer, Jennifer Grimmer, Michael Bolte ORCiD, Georg Manolikakes ORCiD GND
URN:	urn:nbn:de:hebis:30:3-561232
DOI:	https://doi.org/10.1002/anie.201907565
ISSN:	1521-3773
Parent Title (German):	Angewandte Chemie. International edition
Publisher:	Wiley-VCH
Place of publication:	Weinheim
Document Type:	Article
Language:	English
Date of Publication (online):	2019/07/12
Date of first Publication:	2019/07/12
Publishing Institution:	Universitätsbibliothek Johann Christian Senckenberg
Release Date:	2020/09/23
Tag:	Lewis acids; domino reactions; enamides; stereoselective synthesis; tetrahydropyrans
Volume:	58
Page Number:	4
First Page:	13056
Last Page:	13059
Note:	(c) 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Note:	Parallelausgabe: Angew. Chem. 2019, 131, 13190– 13193, Deutsche Ausgabe: DOI: 10.1002/ange.201907565
HeBIS-PPN:	47096099X
Institutes:	Biochemie, Chemie und Pharmazie / Biochemie und Chemie
Dewey Decimal Classification:	5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Sammlungen:	Universitätspublikationen
Licence (German):	Creative Commons - Namensnennung 4.0

Open Access