8.2 Enantioselective Oxidation of Alcohols
Book
Editor: Muniz, K.
Title: Catalytic Oxidation in Organic Synthesis
Print ISBN: 9783132012318; Online ISBN: 9783132403710; Book DOI: 10.1055/b-003-129345
1st edition © 2018. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry
Science of Synthesis Reference Libraries
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Koch, G.; Molander, G. A.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.
Type: Multivolume Edition
Abstract
Described herein is a review of methods for the enantioselective oxidation of alcohol derivatives to afford enantioenriched alcohols from the corresponding racemates. This review emphasizes recent discoveries in the field, i.e. those that have been reported since 2011. Topics covered include transfer hydrogenation, aerobic metal catalysis, nitroxyl-based radical catalysis, manganese catalysis, and biocatalysis.
Key words
alcohols - carbonyl compounds - oxidation - enantioselectivity - stereoselectivity - kinetic resolution - desymmetrization - transfer hydrogenation - aerobic metal catalysis - nitroxyl-based radical catalysis - manganese catalysis - iridium catalysis - palladium catalysis - ruthenium catalysis - iron catalysis - vanadium catalysis - biocatalysis- 1 Stoltz B, Ebner D C, Park N, In Science of Synthesis: Stereoselective Synthesis. Molander G A. Thieme; Stuttgart 2011. Vol. 2, Section 2.4, p 209.
-
8 Hashiguchi S, Fujii A, Haack K-J, Matsumura K, Ikariya T, Noyori R. Angew. Chem. 1997; 109: 300 Angew. Chem. Int. Ed. Engl. 1997; 36: 288
-
20 Arita S, Koike T, Kayaki Y, Ikariya T. Angew. Chem. 2008; 120: 2481 Angew. Chem. Int. Ed. 2008; 47: 2447
-
23 Weng S-S, Shen M-W, Kao J-Q, Munot Y S, Chen C-T. Proc. Natl. Acad. Sci. U. S. A. 2006; 103: 3522
-
32 Ebner D C, Trend R M, Genet C, McGrath M J, OʼBrien P, Stoltz B M. Angew. Chem. 2008; 120: 6467 Angew. Chem. Int. Ed. 2008; 47: 6367
-
40 Ebner D C, Bagdanoff J T, Ferreira E M, McFadden R M, Caspi D D, Trend R M, Stoltz B M. Chem.–Eur. J. 2009; 15: 12978
-
41 Krishnan S, Bagdanoff J T, Ebner D C, Ramtohul Y K, Tambar U K, Stoltz B M. J. Am. Chem. Soc. 2008; 130: 13745
-
46 Mizoguchi H, Uchida T, Katsuki T. Angew. Chem. 2014; 126: 3242 Angew. Chem. Int. Ed. 2014; 53: 3178
-
53 Murakami K, Sasano Y, Tomizawa M, Shibuya M, Kwon E, Iwabuchi Y. J. Am. Chem. Soc. 2014; 136: 17591