Open AccessStereoselective Synthesis of Biologically Relevant Tetrahydropyridines and Dihydro-2H-pyrans via Ring-Expansion of Monocyclopropanated Heterocycles
Author(s) -
Robert Eckl,
Sebastian Fischer,
Carina M. Sonnleitner,
Daniel Schmidhuber,
Julia Rehbein,
Oliver Reiser
Publication year - 2021
Publication title -
acs organic and inorganic au
Language(s) - English
Resource type - Journals
ISSN - 2694-247X
DOI - 10.1021/acsorginorgau.1c00042
Subject(s) - stereoselectivity , cyclopropane , pyran , chemistry , ring (chemistry) , combinatorial chemistry , stereochemistry , enantioselective synthesis , cleavage (geology) , drug discovery , organic chemistry , catalysis , materials science , biochemistry , fracture (geology) , composite material
A stereoselective, scalable, and metal-free ring-expansion of monocyclopropanated pyrroles and furans has been developed, leading to value-added highly functionalized tetrahydropyridine and dihydro-2 H -pyran derivatives. Featuring a cyclopropylcarbinyl cation rearrangement as the key step, the selective cleavage of the unactivated endocyclic cyclopropane C-C bond is achieved. Targeted transformations of the thus obtained six-membered heterocycles give access to versatile building blocks with relevance for drug synthesis.