34.9. 2 β-Fluoro Alcohols (Update 2013)
Book
Editors: Banert, K.; Carreira, E. M.; Marek, I.; Reissig, H.-U.; Steel, P. G.
Title: Knowledge Updates 2013/4
Print ISBN: 9783131728111; Online ISBN: 9783132401464; Book DOI: 10.1055/b-003-128254
1st edition © 2014 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry
Science of Synthesis Knowledge Updates
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Molander, G. A.; Reider, P. J..; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.
Type: Multivolume Edition
Abstract

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of β-fluoro alcohols. It focuses on the literature published in the period 2005–2012. Routes discussed include epoxide opening by fluoride, reduction of α-fluoro ketones, fluoromethylation of aldehydes, and hydroxyfluorination of alkenes. Special attention is given to the stereoselective synthesis of β-fluoro alcohols.
Key words
alkene hydroxyfluorination - asymmetric synthesis - carbon-halogen bonds - carbonyl fluoromethylation - desulfonylation - epoxide ring opening - fluorides - fluorine compounds - β-fluoro alcohols - stereoselective synthesis - transfer hydrogenation- 1 Adam J, Foricher J, Hanlon S, Lohri B, Moine G, Schmid R, Stahr H, Weber M, Wirz B, Zutter U. Org. Process Res. Dev. 2011; 15: 515
- 4 Islas-González G, Puigjaner C, Vidal-Ferran A, Moyano A, Riera A, Pericàs MA. Tetrahedron Lett. 2004; 45: 6337
- 5 Cresswell AJ, Davies SG, Lee JA, Roberts PM, Russell AJ, Thomson JE, Tyte MJ. Org. Lett. 2010; 12: 2936
- 26 Fukuzumi T, Shibata N, Sugiura M, Yasui H, Nakamura S, Toru T. Angew. Chem. Int. Ed. 2006; 45: 4973
- 27 Furukawa T, Goto Y, Kawazoe J, Tokunaga E, Nakamura S, Yang Y, Du H, Kakehi A, Shiro M, Shibata N. Angew. Chem. Int. Ed. 2010; 49: 1642