Journal
SCIENCE
Volume 355, Issue 6324, Pages 499-+Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.aal5175
Keywords
-
Categories
Funding
- Scripps Research Institute
- NIH (National Institute of General Medical Sciences) [2R01GM084019]
- Bristol-Myers Squibb
Ask authors/readers for more resources
The enzymatic beta-C-H hydroxylation of the feedstock chemical isobutyric acid has enabled the asymmetric synthesis of a wide variety of polyketides. The analogous transition metal-catalyzed enantioselective beta-C-H functionalization of isobutyric acid-derived substrates should provide a versatile method for constructing useful building blocks with enantioenriched a-chiral centers from this abundant C-4 skeleton. However, the desymmetrization of ubiquitous isopropyl moieties by organometallic catalysts has remained an unanswered challenge. Herein, we report the design of chiral mono-protected aminomethyl oxazoline ligands that enable desymmetrization of isopropyl groups via palladium insertion into the C(sp(3))-H bonds of one of the prochiral methyl groups. We detail the enantioselective beta-arylation, -alkenylation, and -alkynylation of isobutyric acid/2-aminoisobutyric acid derivatives, which may serve as a platform for the construction of a-chiral centers.
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