Oxodealkenylative Cleavage of Alkene C(sp(3))-C(sp(2)) Bonds: A Practical Method for Introducing Carbonyls into Chiral Pool Materials

Andrew J. Smaligo; Jason Wu; Nikolas R. Burton; Allison S. Hacker; Aslam C. Shaikh; Jason C. Quintana; Ruoxi Wang; Changmin Xie; Ohyun Kwon

doi:10.1002/anie.201913201

Back

Oxodealkenylative Cleavage of Alkene C(sp(3))-C(sp(2)) Bonds: A Practical Method for Introducing Carbonyls into Chiral Pool Materials

Journal article

Peer reviewed

Oxodealkenylative Cleavage of Alkene C(sp(3))-C(sp(2)) Bonds: A Practical Method for Introducing Carbonyls into Chiral Pool Materials

Andrew J. Smaligo, Jason Wu, Nikolas R. Burton, Allison S. Hacker, Aslam C. Shaikh, Jason C. Quintana, Ruoxi Wang, Changmin Xie and Ohyun Kwon

Angewandte Chemie (International ed.), Vol.59(3), pp.1211-1215

13/01/2020

DOI: https://doi.org/10.1002/anie.201913201

PMCID: 6942233

PMID: 31692203

Abstract

Chemistry

Chemistry, Multidisciplinary

Physical Sciences

Science & Technology

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 alpha-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.

Metrics

1 Record Views

See more details

Details

Title: Oxodealkenylative Cleavage of Alkene C(sp(3))-C(sp(2)) Bonds: A Practical Method for Introducing Carbonyls into Chiral Pool Materials
Creators - without role: Andrew J. Smaligo - University of California, Los Angeles
Jason Wu - University of California, Los Angeles
Nikolas R. Burton - University of California, Los Angeles
Allison S. Hacker - University of California, Los Angeles
Aslam C. Shaikh - University of California, Los Angeles
Jason C. Quintana - University of California, Los Angeles
Ruoxi Wang - University of California, Los Angeles
Changmin Xie - University of California, Los Angeles
Ohyun Kwon - University of California, Los Angeles
Publication Details: Angewandte Chemie (International ed.), Vol.59(3), pp.1211-1215
Publisher: Wiley
Number of pages: 5
Grant note: UCLA Dissertation Year Fellowship R01GM071779 / NIH; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA Majeti-Alapati fellowship
Identifiers: 9945679808331
Academic Unit: King Abdullah University of Science & Technology
Language: English
Resource Type: Journal article