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Synlett 2006(5): 0809-0810  
DOI: 10.1055/s-2006-933118
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

tert-Butoxy Bis(dimethyl-amino)methane (Bredereck’s Reagent)

Giovanni Bernardi Rosso*
Instituto de Química, Universidade Estadual de Campinas, ­UNICAMP, C.P. 6154, CEP 13083-970, Campinas, São Paulo, Brasil
e-Mail: gbr_chemistry@yahoo.com.br;
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Publication History

Publication Date:
09 March 2006 (online)

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Introduction

tert-Butoxy-bis(dimethylamino)methane [Bredereck’s reagent, t-BuOCH(NMe2)2] (Figure 1) is a useful reagent for α-methylation, α-methylenation, and α-amination of several carbonyl systems or compounds with an active CH group.

Figure 1 Bredereck’s reagent (1).

Compared to the conventional methods to insert a methyl, methylene or amine groups at the position α to a carbonyl group, Bredereck’s reagent has the advantage of generating a strong basic alkoxide (t-BuO-) in situ and the corresponding iminium ion by thermal decomposition. After the Mannich reaction between the carbonyl substrate and the iminium ion formed in situ, β-elimination of dimethylamine from the adduct in the final step affords the condensation product which can be transformed into various types of compounds as shown below. These factors combine to make Bredereck’s reagent the reagent of choice for α-methylation, α-methylenation, and α-amination of carbonyl compounds.