1,8-Diazabicyclo[5.4.0]undec-7-ene (C15-1298-372)

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. It promotes the methylation reaction of phenols, indoles and benzimidazoles with dimethyl carbonate under mild conditions.

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Application

1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) may be used:

• as catalyst for carboxylic acid esterification with dimethyl carbonate
• in the synthesis of duocarmycin and CC-1065 analogs
• as catalyst in aza-Michael addition and Knovenegal condensation reaction
• 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)
• in a new synthesis of the ABCD ring system of Camptothecin

1,8-Diazabicyclo[5.4.0]undec-7-ene may be used as an catalyst for the dissolution and activation of cellulose by a reversible reaction of its hydroxyl groups with carbon dioxide. This dissolved cellulose system can be derivatized to form cellulose mixed esters.

Used in a new synthesis of the ABCD ring system of Camptothecin.

Features and Benefits

Strong hindered amine base.

Citation

An application review.