Ontology highlight
ABSTRACT:
SUBMITTER: Ebule R
PROVIDER: S-EPMC6482821 | biostudies-literature | 2019 Mar
REPOSITORIES: biostudies-literature
The Journal of organic chemistry 20190227 6
We report that HCl·DMPU induces the formation of (thiomethyl)methyl carbenium ion from DMSO under mild conditions. Homoallylic amines react with this electrophile to generate 4-chloropiperidines in good yields. The method applies to both aromatic and aliphatic amines. The use of HCl·DMPU as both non-nucleophilic base and chloride source constitutes an environmentally benign alternative for piperidine formation. The reaction has a broad substrate scope, and the conditions offer good chemical yiel ...[more]