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Oxodealkenylative Cleavage of Alkene C(sp 3 )−C(sp 2 ) Bonds: A Practical Method for Introducing Carbonyls into Chiral Pool Materials
Author(s) -
Smaligo Andrew J.,
Wu Jason,
Burton Nikolas R.,
Hacker Allison S.,
Shaikh Aslam C.,
Quintana Jason C.,
Wang Ruoxi,
Xie Changmin,
Kwon Ohyun
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201913201
Subject(s) - ozonolysis , chemistry , alkene , oxidative cleavage , alkoxy group , terpene , alkyl , cleavage (geology) , bond cleavage , fragmentation (computing) , medicinal chemistry , organic chemistry , photochemistry , catalysis , fracture (geology) , geotechnical engineering , computer science , engineering , operating system
Reported herein is a one‐pot protocol for the oxodealkenylative introduction of carbonyl functionalities into terpenes and terpene‐derived compounds. This transformation proceeds by Criegee ozonolysis of an alkene, reductive cleavage of the resulting α‐alkoxy hydroperoxide, trapping of the generated alkyl radical with 2,2,6,6‐tetramethylpiperidin‐1‐yl (TEMPO), and subsequent oxidative fragmentation with MMPP. Using readily available starting materials from chiral pool, a variety of carbonyl‐containing products have been accessed rapidly in good yields.