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Stereoselective Synthesis of Spiro‐Azacycles Through Tri‐bromide Mediated Oxidative Dearomatization
Author(s) -
Sahoo Sushree Ranjan,
Sarkar Debayan
Publication year - 2020
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.201901676
Subject(s) - chemistry , stereoselectivity , intramolecular force , bromide , reagent , oxidative phosphorylation , ammonium bromide , organic chemistry , combinatorial chemistry , stereochemistry , medicinal chemistry , catalysis , biochemistry , pulmonary surfactant
A metal‐free one‐pot approach towards a highly stereoselective synthesis of N ‐substituted spiro‐azacyclodienones, dihydro spiro‐azacyclodienones and spiro‐lactams have been reported in this present work. Phenyl tri‐methyl ammonium tri‐bromide (PTAB) as an effective reagent has been employed for intramolecular spiro‐cyclizations via the key oxidative dearomatization reaction. Interestingly, the obtained N ‐substituted spiro‐azacyclodienones was readily transformed into strained cyclopropanated spirocycles.