Diethylaminosulfur Trifluoride (DAST)-Mediated Intramolecular Benzannulation of o-Allylchalcones: Synthesis of 3-Fluorotetralins

Meng-Yang Chang; Han-Yu Chen; Yu-Lin Tsai

doi:10.1055/s-0037-1612419

Synthesis, Table of Contents

Synthesis 2019; 51(12): 2553-2563
DOI: 10.1055/s-0037-1612419

paper

Diethylaminosulfur Trifluoride (DAST)-Mediated Intramolecular Benzannulation of o-Allylchalcones: Synthesis of 3-Fluorotetralins

Meng-Yang Chang *

^aDepartment of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan

^bDepartment of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan Email: mychang@kmu.edu.tw

,

Han-Yu Chen

^aDepartment of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan

,

Yu-Lin Tsai

^aDepartment of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan

› Author Affiliations

Abstract

All articles of this category

Abstract

A concise route for the synthesis of 3-fluorotetralines is described, including: (i) NaBH₄-mediated reduction of oxygenated o-allylchalcones and (ii) sequential DAST-mediated intramolecular annulation of the resulting alkenols. A plausible mechanism is proposed and discussed. This protocol provides highly effective regio- and stereocontrolled allyl-enone cross-coupling to construct two stereocenters and one E-configured styryl group.

Key words

DAST - intramolecular benzannulation - o-allylchalcones - cross-coupling reaction - 3-fluorotetralines

Full Text

References

References
1 Hollingworth C, Gouverneur V. Chem. Commun. 2012; 48: 2929
2 Singh RP, Shreeve JM. Synthesis 2002; 2561
3 Ferreira SB. Synlett 2006; 1130
4 Ferret H, Dechamps I, Pardo D.-G, Hijfte LV, Cossy J. ARKIVOC 2010; (viii): 126

5a Dawood KM. Tetrahedron 2004; 60: 1435
5b Fustero S, Sedgwick DM, Román R, Barrio P. Chem. Commun. 2018; 54: 9706

6 Rozen S. Acc. Chem. Res. 2005; 38: 803
7 Nyffeler PT, Duron SG, Byrkart MD, Vincent SP, Wong CH. Angew. Chem. Int. Ed. 2005; 44: 192

Selected books on organofluorine compounds, see:

8a Filler R, Kobayashi Y. Biomedicinal Aspects of Fluorine Chemistry . Elsevier; Amsterdam: 1982
8b Welch JT, Eswarakrishan S. Fluorine in Bioorganic Chemistry . Wiley; New York: 1991
8c Soloshonok VA. Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenge and Biomedical Targets. Wiley; New York: 1999

9 For fluoro-containing agrochemicals, see: Lang RW. Fluorinated Agrochemicals . In Chemistry of Organofluorine Compounds II, A Critical Review, ACS Monograph Series #187. Hudlicky M, Pavlath AE. American Chemical Society; Washington DC: 1995

Selected examples on synthesis of mono-fluorinated linear skeletons; for benzylic fluorides, see:

10a Cresswell AL, Davies SG, Lee JA, Roberts PM, Russell AJ, Thomson JE, Tyte MJ. Org. Lett. 2010; 12: 2936

For fluorohydrins, see:

10b Islas-Gonzalez G, Puigjaner C, Vidal-Ferran A, Moyano A, Riera A, Pericas MA. Tetrahedron Lett. 2004; 45: 6337

For fluorinated alkanes, see:

10c Kim K.-Y, Kim BC, Lee HB, Shin H. J. Org. Chem. 2008; 73: 8106

Selected examples for the synthesis of 3-fluoropyrrolidines, see:

11a Kitamura T, Miyake A, Muta K, Oyamada J. J. Org. Chem. 2017; 82: 11721
11b Cui J, Jia Q, Feng RZ, Liu S.-S, He T, Zhang C. Org. Lett. 2014; 16: 1442

Selected examples for the synthesis of 4-fluorotetrahydropyrans, see:

12a Al-Mutairi EH, Crosby SR, Darzi J, Harding JR, Hughes RA, King CD, Simpson TJ, Smith RW, Willis CL. Chem. Commun. 2001; 835
12b Kataoka K, Ode Y, Matsumoto M, Nokami J. Tetrahedron 2006; 62: 2471
12c Luo H.-Q, Hu X.-H, Loh T.-P. Tetrahedron Lett. 2010; 51: 1041

Selected examples for the synthesis of 3- or 4-fluoropiperidines, see:

13a Vardelle E, Martin-Mingot A, Jouannetaud M, Bachmann C, Marrot J, Thibaudeau S. J. Org. Chem. 2009; 74: 6025
13b Kishi Y, Nagura H, Inagi S, Fuchigami T. Chem. Commun. 2008; 3876
13c Okoromoba OE, Hammond GB, Xu B. Org. Lett. 2015; 17: 3975

14 Yeh M.-CP, Liang C.-J, Huang T.-L, Hsu H.-J, Tsau Y.-S. J. Org. Chem. 2013; 78: 5521
15 Nonn M, Kiss L, Haukka M, Fustero S, Fülöp F. Org. Lett. 2015; 17: 1074
16 Huang HT, Lacy TC, Blachut B, Ortiz GX. Jr, Wang Q. Org. Lett. 2013; 15: 1818
17 Yan T, Zhou B, Xue XS, Cheng JP. J. Org. Chem. 2016; 81: 9006
18 Li F, Nie J, Wu JW, Zheng Y, Ma JA. J. Org. Chem. 2012; 77: 2398
19 Probst N, Martin A, Désiré J, Mingot A, Marrot J, Blériot Y, Thibaudeau S. Org. Lett. 2017; 19: 1040
20 Yang L, Ma Y, Song F, You J. Chem. Commun. 2014; 50: 3024

21a Lázaro R, Román R, Sedgwick DM, Haufe G, Barrio P, Fustero S. Org. Lett. 2016; 18: 948
21b Masson G, Rioton S, Pardo DG, Cossy J. Org. Lett. 2018; 20: 5019
21c Rioton S, Orliac A, Antoun Z, Bidault R, Pardo DG, Cossy J. Org. Lett. 2015; 17: 2916
21d Remete AM, Nonn M, Fustero S, Haukka M, Fülöp F, Kiss L. Eur. J. Org. Chem. 2018; 3735

22 Review on o-carbonyl allylarenes, see: Hassam M, Taher A, Arnott GE, Green IR, van Otterlo WA. L. Chem. Rev. 2015; 115: 5462
23 Chang M.-Y, Wu M.-H, Tai H.-Y. Org. Lett. 2012; 14: 3936
24 Chang M.-Y, Wu M.-H. Tetrahedron 2013; 69: 129
25 Chang M.-Y, Chan C.-K, Lin S.-Y. Tetrahedron 2013; 69: 1532
26 Chang M.-Y, Wu M.-H, Chen Y.-L. Org. Lett. 2013; 15: 2822
27 Chang M.-Y, Hsiao Y.-T, Lai K.-H. J. Org. Chem. 2018; 83: 14110
28 Chan C.-K, Chan Y.-L, Tsai Y.-L, Chang M.-Y. Tetrahedron 2017; 73: 2074
29 Hsueh N.-C, Chen H.-Y, Chang M.-Y. J. Org. Chem. 2017; 82: 13324
30 Chan C.-K, Tsai Y.-L, Chang M.-Y. Org. Lett. 2017; 19: 1870
31 Chang M.-Y, Tai H.-Y, Chen Y.-L, Hsu R.-T. Tetrahedron 2012; 68: 7941
32 CCDC 1861178 (4g) and 1861180 (5a) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.

33a Pettit GR, Singh SB, Boyd MR, Hamel E, Pettit RK, Schmidt JM, Hogan F. J. Med. Chem. 1995; 38: 1666
33b Gill RK, Kaur R, Kaur G, Rawal RK, Shah AK, Bariwal J. Curr. Org. Chem. 2014; 18: 2462
33c O’Boyle NM, Carr M, Greene LM, Bergin O, Nathwani SM, McCabe T, Lloyd DG, Zisterer DM, Meegan M. J. Med. Chem. 2010; 53: 8569

34 Qin Y, Lv J, Luo S, Cheng J.-P. Org. Lett. 2014; 16: 5032

Supplementary Material