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1,8‐Diazabicyclo[5.4.0]undec‐7‐ene: A Remarkable Base in the Debromination of 4‐ or 5‐Substituted N ‐Benzyl α‐Bromo‐α‐ p ‐Toluenesulfonylglutarimide
Author(s) -
Chang MengYang,
Lin John, YiChung,
Chen ShuiTein,
Chang NeinChen
Publication year - 2002
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200200145
Subject(s) - chemistry , bicyclic molecule , ene reaction , base (topology) , medicinal chemistry , stereochemistry , mathematical analysis , mathematics
Debromination of N ‐benzyl 4‐ or 5‐substituted α‐bromo‐α‐ p ‐toluenesulfonylglutarimides is achieved with 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) to give the N ‐benzyl 4‐ or 5‐substituted α‐ p ‐toluenesulfonylglutarimides. The DBU/THF system is applied to a new methodology for the synthesis of bicyclic glutarimide skeleton in moderate yields.