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Facile Diastereoselective Synthesis of Highly Substituted Alkylene‐oxetanes from 3‐Alkyl Allenoates and Diaryl 1,2‐Diones/α‐Ketoamides Mediated by DBU
Author(s) -
Krishnan Jagadeesh,
Mayadevi T. S.,
Varughese Sunil,
Nair Vijay
Publication year - 2019
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.201801747
Subject(s) - oxetane , chemistry , alkyl , annulation , amide , tertiary amine , amine gas treating , phosphonium , methylene , organic chemistry , medicinal chemistry , catalysis
A facile tertiary amine‐mediated [2+2] annulation reaction of 3‐alkyl allenoates, and diaryl 1,2‐diones leading to diastereoselective synthesis of highly substituted alkylene‐oxetane derivatives is reported. The reaction was further extended to α‐ketoamides. The obtained amide‐appended oxetanes were transformed to 5‐methylene‐1 H ‐pyrrol‐2(5 H )‐one derivatives with potential biological activity.