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From Wikipedia, the free encyclopedia
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 |
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]
Other heterocyclic disulfides have been used in place of 2,2'-dipyridyldisulfide.[6][7][8][9]
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