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Divergent Reactivity of 2‐Azetidinone‐Tethered Allenols with Electrophilic Reagents: Controlled Ring Expansion versus Spirocyclization
Author(s) -
Alcaide Benito,
Almendros Pedro,
Luna Amparo,
Torres M. Rosario
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900864
Subject(s) - chemistry , reagent , electrophile , reactivity (psychology) , ring (chemistry) , combinatorial chemistry , stereochemistry , lactam , organic chemistry , catalysis , medicine , alternative medicine , pathology
A dual reactivity of 2‐azetidinone‐tethered allenols may occur by judicious choice of the electrophilic reagents, namely halogenating versus selenating reagents. Using common substrates, structurally different compounds, namely tetramic acids (from N ‐bromosuccinimide) or spirocyclic seleno‐β‐lactams (from N ‐phenylselenophthalimide), can be readily synthesized by these divergent protocols.