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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201913201
Subject(s) - ozonolysis , alkene , chemistry , alkoxy group , oxidative cleavage , terpene , alkyl , cleavage (geology) , medicinal chemistry , organic chemistry , bond cleavage , fragmentation (computing) , stereochemistry , catalysis , materials science , fracture (geology) , computer science , composite material , 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.