Keck macrolactonization

What is Keck macrolactonization?

Keck macrolactonization is the formation of a macrolactone through esterification using a carbodiimide, such as DCC, was initially documented by Keck in 1985. To facilitate this reaction, a nitrogenous base, like DMAP or N,N-dimethylalanine, is required (see list of acronyms).

Keck macrolactonization - general reaction scheme
Keck macrolactonization

Due to its widespread use in synthesizing a range of macrolactones, this method is now referred to as the Keck macrolactonization.


Proton-transfer steps in Steglich esterification: a very practical new method for macrolactonization
Eugene P. Boden and Gary E. Keck
The Journal of Organic Chemistry 1985 50 (13), 2394-2395
DOI: 10.1021/jo00213a044