Corey–Nicolaou macrolactonization
Chemical reaction
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Corey–Nicolaou macrolactonization is a named reaction of organic chemistry, for the synthesis of lactones from hydroxy acids, found in 1974.[1][2] The reaction uses 2,2'-dipyridyldisulfide and triphenylphosphine as reagents and runs in polar aprotic solvent under mild conditions.[3]
| Corey–Nicolaou macrolactonization | |
|---|---|
| Named after | Elias James Corey K. C. Nicolaou |
| Reaction type | Name reaction |
Mechanism
The hydroxy acid first reacts with the 2,2'-Dipyridyldisulfide to form the corresponding 2-pyridinethiol ester, and after a proton transfer, the alkoxide attacks the carbonyl carbon, forming a tetrahedral transition state, before resolving back to the desired lactone and 2-pyridinethione.[4][5]
