- Natural-, Medical- , Computer Sciences, Technology
- Chemistry
- Organic chemistry
- Organocatalytic Approaches to Asymmetric Oxidation
- Bookcover of Organocatalytic Approaches to Asymmetric Oxidation
- Booktitle:
-
Organocatalytic Approaches to Asymmetric Oxidation
Epoxidation of α-Branched Enals and α-Benzoyloxylation of Carbonyl Compounds
LAP LAMBERT Academic Publishing (2015-05-08 )
eligible for voucher
- ISBN-13:
978-3-659-69254-3
- ISBN-10:
- 3659692549
- EAN:
- 9783659692543
- Book language:
- Blurb/Shorttext:
- This work describes the development of enantioselective oxidation reactions of carbonyl compounds using covalent organocatalysis. In the first part, asymmetric epoxidation of α-branched α,β-unsaturated aldehydes with aqueous hydrogen peroxide is presented. An exceptionally synergistic combination of a primary cinchona alkaloid-derived amine and a chiral BINOL-derived phosphoric acid was found to promote the reaction with excellent enantiocontrol for a wide variety of α,β-disubstituted and α-monosubstituted enals. Conformational analysis of catalytically relevant intermediates using NMR and computational techniques enabled the rationalization of the absolute stereochemistry of products. The second part of this book describes a highly efficient direct catalytic asymmetric α-benzoyloxylation of cyclic ketones. The same primary amine paired with an inorganic acid was found to be an effective catalyst for a wide range of substrates. The methodology was applied to the first asymmetric synthesis of (+)-2β,4-dihydroxy-1,8-cineole, a predicted terpenoid metabolite in mammals.
- Publishing house:
- LAP LAMBERT Academic Publishing
- Website:
- https://www.lap-publishing.com/
- By (author) :
- Olga Schöne
- Number of pages:
- 256
- Published at:
- 2015-05-08
- Stock:
- Available
- Category:
- Organic chemistry
- Price:
- 76.90 €
- Keywords:
- Epoxidation, aminocatalysis, ACDC, α-oxidation, Asymmetric Catalysis, Organocatalysis
