Cyclic guanidine organic catalysts: What is magic about triazabicyclodecene?

…, RL Weber, JL Hedrick, RM Waymouth

文献索引：Kiesewetter, Matthew K.; Scholten, Marc D.; Kirn, Nicole; Weber, Ryan L.; Hedrick, James L.; Waymouth, Robert M. Journal of Organic Chemistry, 2009 , vol. 74, # 24 p. 9490 - 9496

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被引用次数: 97

摘要

The bicyclic guanidine 1, 5, 7-triazabicyclo [4.4. 0] dec-5-ene (TBD) is an effective organocatalyst for the formation of amides from esters and primary amines. Mechanistic and kinetic investigations support a nucleophilic mechanism where TBD reacts reversibly with esters to generate an acyl-TBD intermediate that acylates amines to generate the amides. Comparative investigations of the analogous bicyclic guanidine 1, 4, 6-triazabicyclo [3.3. 0 ...