Format:
Online-Ressource
ISSN:
1099-0690
Content:
Abstract: Preparation of piperidine‐2‐one scaffolds by the hetero‐Diels–Alder (HAD) reaction, assisted by microwaves, is described. The versatility of this new approach has been demonstrated by the synthesis of racemic (±)‐2‐phenylpiperidine. Theoretical calculations have allowed us to clarify the factors that govern ring closure to form four‐membered rings, arising from a Staudinger‐type electrocyclization, and/or six‐membered rings through a classical [4+2] HAD cyclization. This competition may be lowered by increasing the electronic demand of the dienophile, as anticipated by the computational studies.
In:
volume:2011
In:
number:31
In:
year:2011
In:
pages:6218-6225
In:
extent:8
In:
European journal of organic chemistry, Weinheim : Wiley-VCH Verl., 1998-, 2011, Heft 31 (2011), 6218-6225 (gesamt 8), 1099-0690
Language:
English
DOI:
10.1002/ejoc.201100930
URN:
urn:nbn:de:101:1-2023031907085274856736
URL:
https://doi.org/10.1002/ejoc.201100930
URL:
https://nbn-resolving.org/urn:nbn:de:101:1-2023031907085274856736
URL:
https://d-nb.info/128379280X/34
URL:
https://doi.org/10.1002/ejoc.201100930