1,8-Diazabicyclo[5.4.0]undec-7-ene

Description

• General description: 1,8-Diazabicyclo[5.4.0]undec-7-ene is a bicyclic amidine base. It is non-nucleophilic, sterically hindered, tertiary amine base in organic chemistry. It is reported to be superior to amine catalyst in Baylis-Hillman reaction.[1] It promotes the methylation reaction of phenols, indoles and benzimidazoles with dimethyl carbonate under mild conditions.[2]
• Application: 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) may be used:as catalyst for carboxylic acid esterification with dimethyl carbonate[3] in the synthesis of duocarmycin and CC-1065 analogs[1] as catalyst in aza-Michael addition[4] and Knovenegal condensation reaction[5]as base for dehalogenation of halogenated Diels-Alder adducts and the resulting activated 2,4-dienones were subjected to regio- and stereo-directed Michael additions, using Yamamoto′s reagent (CH3Cu · BF3)[6]in a new synthesis of the ABCD ring system of Camptothecin[7]
• Features and Benefits: Strong hindered amine base.
• Citation: An application review.[10]