6 Chemoenzymatic Dynamic Kinetic Resolution of Alcohols
Book
Editor: Bäckvall, J.-E.
Title: Dynamic Kinetic Resolution (DKR) and Dynamic Kinetic Asymmetric Transformations (DYKAT)
Print ISBN: 9783132453777; Online ISBN: 9783132453791; Book DOI: 10.1055/b000000439
2023 © 2023. 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.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.
Type: Multivolume Edition
Abstract
Chemoenzymatic dynamic kinetic resolution is one of the simplest and most reliable methods to obtain optically pure alcohol derivatives from racemates. For this purpose, hydrolases, especially lipases, have been widely used in the enantioselective esterification processes, and a variety of racemization catalysts with high catalytic efficiency and compatibility with lipases have been developed. This review introduces chemoenzymatic DKR of alcohols based on the category of racemization catalysts. DKR of axially chiral hydroxybiaryls and the use of engineered lipases to obtain opposite enantiomers, as well as the synthetic applications of the DKR products, are also discussed.
Key words
lipase - hydrolase - racemization - asymmetric synthesis - total synthesis - alcohols - acylation - esterification - dynamic kinetic resolution - enantioselectivity - ruthenium - oxovanadium- 8 Akai S, Moustafa GAI, Kinetic Control in Synthesis and Self-Assembly. Numata M, Yagai S, Hamura T. Academic; London 2019
-
22 Mavrynsky D, Päiviö M, Lundell K, Sillanpää R, Kanerva LT, Leino R. Eur. J. Org. Chem. 2009; 1317
-
40 van Nispen SFGM, van Buijtenen J, Vekemans JAJM, Meuldijk J, Hulshof LA. Tetrahedron: Asymmetry 2006; 17: 2299
-
44 Wieczorek B, Träff A, Krumlinde P, Dijkstra HP, Egmond MR, van Koten G, Bäckvall J.-E, Klein Gebbink RJM. Tetrahedron Lett. 2011; 52: 1601
-
50 Långvik O, Saloranta T, Kirilin A, Liljeblad A, Mäki-Arvela P, Kanerva LT, Murzin DY, Leino R. ChemCatChem 2010; 2: 1615
-
67 Kiełbasiński P, Rachwalski M, Mikołajczyk M, Moelands MAH, Zwanenburg B, Rutjes FPJT. Tetrahedron: Asymmetry 2005; 16: 2157
-
69 Thalén LK, Sumic A, Bogár K, Norinder J, Persson AKÅ, Bäckvall J.-E. J. Org. Chem. 2010; 75: 6842
-
87 Kasama K, Kanomata K, Hinami Y, Mizuno K, Uetake Y, Amaya T, Sako M, Takizawa S, Sasai H, Akai S. RSC Adv. 2021; 11: 35342
-
90 de Miranda AS, de M. Silva MV, Dias FC, de Souza SP, Leão RAC, de Souza ROMA. React. Chem. Eng. 2017; 2: 375
-
93 Sugiyama K, Oki Y, Kawanishi S, Kato K, Ikawa T, Egi M, Akai S. Catal. Sci. Technol. 2016; 6: 5023
-
95 Higashio K, Katsuragi S, Kundu D, Adebar N, Plass C, Kühn F, Gröger H, Akai S. Eur. J. Org. Chem. 2020; 1961
-
107 Haak RM, Berthiol F, Jerphagnon T, Gayet AJA, Tarabiono C, Postema CP, Ritleng V, Pfeffer M, Janssen DB, Minnaard AJ, Feringa BL, de Vries JG. J. Am. Chem. Soc. 2008; 130: 13508
-
109 Haak RM, Tarabiono C, Janssen DB, Minnaard AJ, de Vries JG, Feringa BL. Org. Biomol. Chem. 2007; 5: 318
-
127 Tsuchimochi I, Hori S, Takeuchi Y, Egi M, Satoh T.-o, Kanomata K, Ikawa T, Akai S. Synlett 2021; 32: 822