TY  - JOUR
A1  - Kramer, Philipp
A1  - Grimmer, Jennifer
A1  - Bolte, Michael
A1  - Manolikakes, Georg
T1  - An enamide‐based domino reaction for a highly stereoselective synthesis of tetrahydropyrans
T2  - Angewandte Chemie. International edition
N2  - 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.
N2  - 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.
KW  - domino reactions
KW  - enamides
KW  - Lewis acids
KW  - stereoselective synthesis
KW  - tetrahydropyrans
Y1  - 2019
UR  - http://publikationen.ub.uni-frankfurt.de/frontdoor/index/index/docId/56123
UR  - https://nbn-resolving.org/urn:nbn:de:hebis:30:3-561232
SN  - 1521-3773
N1  - (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.
N1  - Parallelausgabe: Angew. Chem. 2019, 131, 13190– 13193, Deutsche Ausgabe: DOI: 10.1002/ange.201907565
VL  - 58
SP  - 13056
EP  - 13059
PB  - Wiley-VCH
CY  - Weinheim
ER  -