Formation of α-SF5-Enolate Enables Preparation of 3-SF5-Quinolin-2-ones, 3-SF5-Quinolines, and 3-SF5-Pyridin-2-ones: Evaluation of their Physicochemical Properties
This study describes, for the first time, the generation of a SF5‐substituted ester enolate from benzyl SF5‐acetate under soft enolization conditions, which in turn participates in aldol addition reactions in high yield. The reaction was applied in the synthesis of 3‐SF5‐quinolin‐2‐ones, 3‐SF5‐quino...
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| Published in | Angewandte Chemie Vol. 128; no. 6; pp. 2153 - 2157 |
|---|---|
| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
Blackwell Publishing Ltd
05.02.2016
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| Subjects | |
| Online Access | Get full text |
| ISSN | 0044-8249 1521-3757 |
| DOI | 10.1002/ange.201510380 |
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| Abstract | This study describes, for the first time, the generation of a SF5‐substituted ester enolate from benzyl SF5‐acetate under soft enolization conditions, which in turn participates in aldol addition reactions in high yield. The reaction was applied in the synthesis of 3‐SF5‐quinolin‐2‐ones, 3‐SF5‐quinolines, and 3‐SF5‐pyridin‐2‐ones, none of which have previously been reported. To provide guidelines for their use in drug discovery, the physicochemical properties of these building blocks were determined and compared with those of their CF3‐ and t‐Bu‐analogues.
SF5 leicht eingeführt: Aldolreaktionen von Enolaten, die in α‐Stellung zu einer Pentafluorsulfanyl‐Gruppe erzeugt wurden, lieferten SF5‐substituierte Heterocyclen in hervorragenden Ausbeuten. Ein Vergleich der physikochemischen Daten mit denen ihrer Trifluormethyl‐ und tert‐Butyl‐Analoga bestätigt, dass die SF5‐Gruppe ein Surrogat für CF3‐ und t‐Bu‐Gruppen darstellt und eine Feineinstellung von Eigenschaften ermöglichen könnte. |
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| AbstractList | This study describes, for the first time, the generation of a SF5‐substituted ester enolate from benzyl SF5‐acetate under soft enolization conditions, which in turn participates in aldol addition reactions in high yield. The reaction was applied in the synthesis of 3‐SF5‐quinolin‐2‐ones, 3‐SF5‐quinolines, and 3‐SF5‐pyridin‐2‐ones, none of which have previously been reported. To provide guidelines for their use in drug discovery, the physicochemical properties of these building blocks were determined and compared with those of their CF3‐ and t‐Bu‐analogues.
SF5 leicht eingeführt: Aldolreaktionen von Enolaten, die in α‐Stellung zu einer Pentafluorsulfanyl‐Gruppe erzeugt wurden, lieferten SF5‐substituierte Heterocyclen in hervorragenden Ausbeuten. Ein Vergleich der physikochemischen Daten mit denen ihrer Trifluormethyl‐ und tert‐Butyl‐Analoga bestätigt, dass die SF5‐Gruppe ein Surrogat für CF3‐ und t‐Bu‐Gruppen darstellt und eine Feineinstellung von Eigenschaften ermöglichen könnte. |
| Author | Joliton, Adrien Plancher, Jean-Marc Carreira, Erick M. |
| Author_xml | – sequence: 1 givenname: Adrien surname: Joliton fullname: Joliton, Adrien organization: Laboratorium für Organische Chemie, ETH Zürich, HCI H335, Vladimir-Prelog-Weg 3, 8093, Zürich, Switzerland – sequence: 2 givenname: Jean-Marc surname: Plancher fullname: Plancher, Jean-Marc organization: Pharmaceutical Research and Early Development, Roche Innovation Center Basel, F. Hoffmann-La Roche Ltd., Grenzacherstrasse 124, 4070, Basel, Switzerland – sequence: 3 givenname: Erick M. surname: Carreira fullname: Carreira, Erick M. email: carreira@org.chem.ethz.ch organization: Laboratorium für Organische Chemie, ETH Zürich, HCI H335, Vladimir-Prelog-Weg 3, 8093, Zürich, Switzerland |
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| References_xml | – reference: Y. Fujiwara, J. A. Dixon, F. O'Hara, E. D. Funder, D. D. Dixon, R. A. Rodriguez, R. D. Baxter, B. Herle, N. Sach, M. R. Collins, Y. Ishihara, P. S. Baran, Nature 2012, 492, 95-99; – reference: J. A. Burkhard, B. Wagner, H. Fischer, F. Schuler, K. Muller, E. M. Carreira, Angew. Chem. Int. Ed. 2010, 49, 3524-3527; – reference: T. Abe, G.-H. Tao, Y.-H. Joo, R. W. Winter, G. L. Gard, J. M. Shreeve, Chem. Eur. J. 2009, 15, 9897-9904; – reference: A. Lishchynskyi, V. V. Grushin, J. Am. Chem. Soc. 2013, 135, 12584-12587; – reference: W. A. Sheppard, J. Am. Chem. Soc. 1962, 84, 3064-3072. – reference: P. Beier, T. Pastýříková, Beilstein J. Org. Chem. 2013, 9, 411-416; – reference: Angew. Chem. 1978, 90, 547-549; – reference: Angew. Chem. 2013, 125, 3541-3544; – reference: S. Garg, J. M. Shreeve, J. Mater. Chem. 2011, 21, 4787-4795; – reference: X. Mi, J. Chen, L. Xu, Eur. J. Org. Chem. 2015, 1415-1418. – reference: Angew. Chem. 2013, 125, 8130-8133; – reference: A. L. Dreier, A. V. Matsnev, J. S. Thrasher, G. Haufe, J. Fluorine Chem. 2014, 167, 84-90. – reference: N. D. Litvinas, P. S. Fier, J. F. Hartwig, Angew. Chem. Int. Ed. 2012, 51, 536-539; – reference: A. Joliton, E. M. Carreira, Org. Lett. 2013, 15, 5147-5149; – reference: B. Poetter, K. Seppelt, Inorg. Chem. 1982, 21, 3147-3150; – reference: Angew. Chem. 1987, 99, 808-810; – reference: G. Danoun, B. Bayarmagnai, M. F. Grunberg, L. J. Goossen, Angew. Chem. Int. Ed. 2013, 52, 7972-7975; – reference: Y. Ye, M. S. Sanford, J. Am. Chem. Soc. 2012, 134, 9034-9037; – reference: T. Bootwicha, X. Liu, R. Pluta, I. Atodiresei, M. Rueping, Angew. Chem. Int. Ed. 2013, 52, 12856-12859; – reference: Angew. Chem. 2015, 127, 282-286. – reference: Angew. Chem. 2013, 125, 8372-8423; for recent examples, see: – reference: Angew. Chem. 2014, 126, 14787-14791; – reference: G. Wuitschik, M. Roger-Evans, A. Buckl, M. Bernasconi, M. Märki, T. Godel, H. Fisher, B. 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| SubjectTerms | Aldolreaktionen Bor Heterocyclen Pentafluorsulfanyl Physikochemische Eigenschaften |
| Title | Formation of α-SF5-Enolate Enables Preparation of 3-SF5-Quinolin-2-ones, 3-SF5-Quinolines, and 3-SF5-Pyridin-2-ones: Evaluation of their Physicochemical Properties |
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