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J Am Chem Soc. 2014 Oct 8;136(40):14019-22. doi: 10.1021/ja508757g. Epub 2014 Sep 29.

Catalyst control over regio- and enantioselectivity in Baeyer-Villiger oxidations of functionalized ketones.

Author information

1
Department of Chemistry, Yale University , 225 Prospect Street, New Haven, Connecticut 06520-8107, United States.

Abstract

We report a peptide-based catalyst that can strongly influence the regio- and enantioselectivity of the Baeyer-Villiger (BV) oxidation of cyclic ketones bearing amide, urea, or sulfonamide functional groups. Both types of selectivity are thought to arise from a catalyst-substrate hydrogen-bonding interaction. Furthermore, in selected cases, the reactions exhibit the hallmarks of parallel kinetic resolution. The capacity to use catalysis to select between BV products during an asymmetric process may have broad utility for both the synthesis and diversification of complex molecules, including natural products.

PMID:
25250713
PMCID:
PMC4195385
DOI:
10.1021/ja508757g
[Indexed for MEDLINE]
Free PMC Article

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