Premium
Densely Functionalized 2‐Methylideneazetidines from Nitrodienic Building Blocks
Author(s) -
Tavani Cinzia,
Bianchi Lara,
Giorgi Gianluca,
Maccagno Massimo,
Petrillo Giovanni
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701467
Subject(s) - chemistry , ring (chemistry) , primary (astronomy) , michael reaction , stereochemistry , combinatorial chemistry , catalysis , organic chemistry , physics , astronomy
Novel, densely functionalized 2‐methylideneazetidines can be obtained in high yields under mild conditions from the reactions of nitropentadienoates with primary amines, most likely through an aza‐Michael addition followed by a 4‐ exo‐trig cyclization. The initial, selective trans arrangement of the C3 and C4 ring hydrogens undergoes stereomutation due to the presence of an easily enolizable site at C3, eventually leading to mixtures in which the cis isomer generally prevails.