Enantioselective Synthesis of 4,4′-Biaryl-BINOLs from Arynes and β-Diketones

Kentaro Okuma; Kenta Horigami; Noriyoshi Nagahora; Kosei Shioji

doi:10.1055/s-0034-1380452

Synthesis, Table of Contents

Synthesis 2015; 47(19): 2937-2944
DOI: 10.1055/s-0034-1380452

special topic

Enantioselective Synthesis of 4,4′-Biaryl-BINOLs from Arynes and β-Diketones

Kentaro Okuma*

Department of Chemistry, Fukuoka University, Jonan-ku, Fukuoka 814-0180, Japan Email: kokuma@fukuoka-u.ac.jp

,

Kenta Horigami

Department of Chemistry, Fukuoka University, Jonan-ku, Fukuoka 814-0180, Japan Email: kokuma@fukuoka-u.ac.jp

,

Noriyoshi Nagahora

Department of Chemistry, Fukuoka University, Jonan-ku, Fukuoka 814-0180, Japan Email: kokuma@fukuoka-u.ac.jp

,

Kosei Shioji

Department of Chemistry, Fukuoka University, Jonan-ku, Fukuoka 814-0180, Japan Email: kokuma@fukuoka-u.ac.jp

› Author Affiliations

Abstract

All articles of this category

Abstract

The reaction of 2-(trimethylsilyl)phenyl triflate with aroylacetones in the presence of CsF gave the corresponding 4-aryl-2-naphthols. Substituted triflates also reacted with aroylacetones to afford 4-aryl-2-naphthols regioselectively. The enantioselective oxidation of 4-aryl-2-naphthols with a chiral tridentate oxovanadium(IV) complex furnished the corresponding 4,4′-biaryl-1,1′-binaphthols in good yields.

Key words

aryne - β-diketone - carbon–carbon bond insertion - 4-aryl-2-naphthol - BINOL

Full Text

References

References

1a Hoffman RW. Dehydrobenzene and Cycloalkynes . Academic Press; New York: 1967
1b Kessar SV In Comprehensive Organic Synthesis . Vol. 4. Trost BM, Fleming I. Pergamon; Oxford: 1991: 483-515
1c Hart H In The Chemistry of Triple-Bonded Functional Groups, Supplement C2. Patai S. Wiley; Chichester: 1994. Chap. 18
1d Wentrup C. Aust. J. Chem. 2010; 63: 979
1e Kitamura T. Aust. J. Chem. 2010; 63: 987

2 Himeshima Y, Sonoda T, Kobayashi H. Chem. Lett. 1983; 1211

3a Okuma K, Okada A, Koga Y, Yokomori Y. J. Am. Chem. Soc. 2001; 123: 7166
3b Yoshida H, Shirakawa E, Honda Y, Hiyama T. Angew. Chem. Int. Ed. 2002; 41: 3247
3c Yoshida H, Fukushima H, Ohshita J, Kunai A. J. Am. Chem. Soc. 2006; 128: 11040
3d Gilmore CD, Allan KM, Stoltz BM. J. Am. Chem. Soc. 2008; 130: 1558

4a Tamber UK, Stoltz BM. J. Am. Chem. Soc. 2005; 127: 5340
4b Yoshida H, Watanabe M, Ohshita J, Kunai A. Chem. Commun. 2005; 3292

5a Kilian P, Knight F, Fergus R, Woollins JD. Chem. Eur. J. 2011; 17: 2302
5b Simon S, Petrasek J. Plant Sci. 2011; 180: 454
5c Cai YS, Guo YW, Krohn K. Nat. Prod. Rep. 2010; 27: 1840
5d Qian X, Xiao Y, Xu Y, Guo X, Qian J, Zhu W. Chem. Commun. 2010; 46: 6418

6a Jin T, Yamamoto Y. Org. Lett. 2007; 9: 5259
6b Rupard JH, Paulis TD, Janowsky A, Smith HE. J. Med. Chem. 1989; 32: 2261
6c Zhangm X, Sarkar S, Larock RC. J. Org. Chem. 2006; 71: 236
6d Nishii Y, Tanabe Y. Tetrahedron Lett. 1995; 36: 8803

7a Kim HY, Oh K. Org. Lett. 2014; 16: 5934
7b Koptyug VA, Andreeva TP. Z. Org. Khim. 1971; 7: 2398 ; Chem. Abstr. 1972, 76, 140286

8 Karady S, Amato JS, Reamer RA, Weinstock LM. Tetrahedron Lett. 1996; 37: 8277
9 Zhang J, Liu Q, Liu X, Zhang S, Jiang P, Wang Y, Luo S, Li Y, Wang Q. Chem. Commun. 2015; 51: 1297

10a Okuma K, Itoyama R, Sou A, Nagahora N, Shioji K. Chem. Commun. 2012; 48: 11145
10b Recently, Wieting et al. reported the synthesis of BINOL 6a by using our method: Wieting JM, Fisher TJ, Schafer AG, Visaco MD, Gallucci JC, Mattson AE. Eur. J. Org. Chem. 2015; 525

11a Mikami K, Shimizu M. Chem. Rev. 1992; 92: 1021
11b Comprehensive Asymmetric Catalysis . Jacobsen EN, Pfaltz A, Yamamoto H. Springer-Verlag; Berlin: 1999
11c Bolm C, Hildebrand JP, Muniz K, Hermanns N. Angew. Chem. Int. Ed. 2001; 40: 3285
11d Irie R, Masutani K, Katsuki T. Synlett 2000; 1433
11e Tashiro A, Mitsuishi A, Irie R, Katsuki T. Synlett 2003; 1868

12a Rauniyar V, Hall DG. Synthesis 2007; 3421
12b Ma L, Mihalcik DJ, Lin W. J. Am. Chem. Soc. 2009; 131: 4610
12c Hashimoto T, Tanaka Y, Maruoka K. Tetrahedron: Asymmetry 2003; 14: 1599

13 Brussee J, Groenendijk JL. G, te Koppele JM, Jansen AC. A. Tetrahedron 1985; 41: 3313
14 Hon S.-W, Li C.-H, Kuo J.-H, Barahate NB, Liu Y.-H, Wang Y, Chen C.-T. Org. Lett. 2001; 3: 869
15 Hu X, Shan Z, Chang Q. Tetrahedron: Asymmetry 2012; 23: 1327
16 Redic R, Schuster GB. J. Photochem. Photobiol. A 2006; 179: 66
17 Lou Z, Zhang S, Chen C, Pang X, Li M, Wen L. Adv. Synth. Catal. 2014; 356: 153
18 Frigoli M, Moustrou C, Samat A, Gugliemetti R. Eur. J. Org. Chem. 2003; 2799
19 Chow HF, Wan CW. J. Org. Chem. 2001; 66: 5042

Supplementary Material

Supporting Information