Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 22, Pages 3983-3989Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201700637
Keywords
biocatalysis; chemical auxiliaries; cytochrome P450 3A4; epoxidation; theobromine
Categories
Funding
- National Science and Engineering Research Council of Canada (NSERC)
- Center in Green Chemistry and Catalysis (CGCC)
- CGCC
- Dr. Richard H. Tomlinson Foundation
Ask authors/readers for more resources
N-Protected beta- and gamma-amino epoxides are useful chiral synthons. We report here that the enzyme cytochrome P450 3A4 can catalyze the formation of such compounds in a regio- and stereoselective manner, even in the presence of multiple double bonds or aromatic substituents. To this end, the theobromine chemical auxiliary is used not only to control the selectivity of the enzyme, but also as a masked amine, and to facilitate product recovery. Theobromine predictably directed epoxidation at the double bond of the fourth carbon from the theobromine group. Unlike with most catalysts, the selectivity did not depend on electronic or steric factors but rather on the position of the olefin relative to the theobromine group.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available