Divergent Reactivity of 2‐Azetidinone‐Tethered Allenols with Electrophilic Reagents: Controlled Ring Expansion  versus  Spirocyclization | Zendy

Alcaide Benito | Zendy; Almendros Pedro | Zendy; Luna Amparo | Zendy; Torres M. Rosario | Zendy

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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.

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