Synthesis of New Axially Chiral Iodoarenes

Mathieu Bekkaye; Géraldine Masson

doi:10.1055/s-0035-1560512

Synthesis, Inhaltsverzeichnis

Synthesis 2016; 48(02): 302-312
DOI: 10.1055/s-0035-1560512

paper

Synthesis of New Axially Chiral Iodoarenes

Mathieu Bekkaye

Institut de Chimie des Substances Naturelles CNRS, Univ. Paris-Sud, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France eMail: geraldine.masson@cnrs.fr

,

Géraldine Masson*

Institut de Chimie des Substances Naturelles CNRS, Univ. Paris-Sud, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France eMail: geraldine.masson@cnrs.fr

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Abstract

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Abstract

A new family of axially chiral iodoarenes derived from commercially available (R)-1,1′-binaphthyl-2,2′-diamine have been synthesized and employed as catalysts in Kita’s enantioselective oxidative spirolactonization of propanoic acid tethered 1-naphthol. Through this study, we explored the relationship between the hypervalent iodoarene geometry and enantioselectivity, contributing to the current understanding of axial-to-central chirality transfer in organoiodine(III) catalysis.

Key words

chiral iodane - hypervalent iodine - dearomatization - stereoselective synthesis - spirolactonization

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References

For reviews, see:

1a Ortiz FL, Iglesias MJ, Fernández I, Sánchez CM. A, Ruiz Gómez G. Chem. Rev. 2007; 107: 1580
1b Quideau S, Pouységu L, Deffieux D. Synlett 2008; 467
1c Hudlicky T, Reed JW. Synlett 2009; 685
1d Roche SP, Porco JA. Angew. Chem. Int. Ed. 2011; 50: 4068
1e Zhuo C.-X, Zhang W, You S.-L. Angew. Chem. Int. Ed. 2012; 51: 12662
1f Ciufolini MA. Can. J. Chem. 2014; 92: 186
1g Harned AM. Tetrahedron Lett. 2014; 55: 4681
1h Maertens G, L’Homme C, Canesi S. Front. Chem. 2015; 2: 115

For reviews on hypervalent iodine chemistry, see:

2a Ciufolini MA, Braun NA, Canesi S, Ousmer M, Chang J, Chai D. Synthesis 2007; 3759
2b Zhdankin VV, Stang PJ. Chem. Rev. 2008; 108: 5299
2c Ochiai M, Miyamoto K. Eur. J. Org. Chem. 2008; 4229
2d Dohi T, Kita Y. Chem. Commun. 2009; 2073
2e Uyanik M, Ishihara K. Chem. Commun. 2009; 2086
2f Ngatimin M, Lupton DW. Aust. J. Chem. 2010; 63: 653
2g Liang H, Ciufolini MA. Angew. Chem. Int. Ed. 2011; 50: 11849
2h Kita Y, Dohi T, Morimoto K. J. Synth. Org. Chem., Jpn. 2011; 69: 1241
2i Fernández González D, Benfatti F, Waser J. ChemCatChem 2012; 4: 955
2j Yusubov MS, Zhdankin VV. Curr. Org. Synth. 2012; 9: 247
2k Farid U, Wirth T In Asymmetric Synthesis II . Christmann M, Bräse S. Wiley-VCH; Weinheim: 2012: 197
2l Brown M, Farid U, Wirth T. Synlett 2013; 24: 424
2m Parra A, Reboredo S. Chem. Eur. J. 2013; 19: 17244
2n Singh FV, Wirth T. Chem. Asian J. 2014; 9: 950
2o Kumar R, Wirth T. Top. Curr. Chem. 2015; doi: 10.1007/128_2015_639

For seminal electrochemical oxidations of iodoarenes, see:

3a Fuchigami T, Fujita T. J. Org. Chem. 1994; 59: 7190
3b Fujita T, Fuchigami T. Tetrahedron Lett. 1996; 37: 4725

Seminal oxidations of iodoarenes using chemical oxidants, see:

3c McKillop A, Kemp D. Tetrahedron 1989; 45: 3299
3d Kazmierczak P, Skulski L, Kraszkiewicz L. Molecules 2001; 6: 881
3e Zielinska A, Skulski L. Molecules 2002; 7: 806
3f Sharefkin JG, Saltzman H. Org. Synth. 1963; 43: 62
3g Zielinska A, Skulski L. Molecules 2005; 10: 190
3h Ochiai M, Takeuchi Y, Katayama T, Sueda T, Miyamoto K. J. Am. Chem. Soc. 2005; 127: 12244
3i Hossain MD, Kitamura T. J. Org. Chem. 2005; 70: 6984
3j Hossain MD, Kitamura T. Bull. Chem. Soc. Jpn. 2006; 79: 142

4a Dohi T, Maruyama A, Takenaga N, Senami K, Minamitsuji Y, Fujioka H, Caemmerer SB, Kita Y. Angew. Chem. Int. Ed. 2008; 47: 3787
4b Dohi T, Takenaga N, Nakae T, Toyoda Y, Yamasaki M, Shiro M, Fujioka H, Maruyama A, Kita Y. J. Am. Chem. Soc. 2013; 135: 4558
4c Uyanik M, Yasui T, Ishihara K. Angew. Chem. Int. Ed. 2010; 49: 2175
4d Uyanik M, Yasui T, Ishihara K. Tetrahedron 2010; 66: 5841
4e Murray SJ, Ibrahim H. Chem. Commun. 2015; 51: 2376
4f Uyanik M, Sasakura N, Kaneko E, Ohori K, Ishihara K. Chem. Lett. 2015; 44: 179

5a Guilbault A.-A, Basdevant B, Wanie V, Legault CY. J. Org. Chem. 2012; 77: 11283
5b Volp KA, Harned AM. Chem. Commun. 2013; 49: 3001
5c Brenet S, Berthiol F, Einhorn J. Eur. J. Org. Chem. 2013; 8094

Examples of chiral hypervalent iodide(III) compounds, see:

6a Imamoto T, Koto H. Chem. Lett. 1986; 15: 967
6b Hatzigrigoriou E, Varvoglis A, Bakola-Christianopoulou M. J. Org. Chem 1990; 55: 315
6c Ray DG, Koser GF. J. Am. Chem. Soc. 1990; 112: 5672
6d Ochiai M, Takaoka Y, Masaki Y, Nagao Y, Shiro M. J. Am. Chem. Soc. 1990; 112: 5677
6e Ray DG, Koser GF. J. Org. Chem. 1992; 57: 1607
6f Rabah GA, Koser GF. Tetrahedron Lett. 1996; 37: 6453
6g Wirth T, Hirt UH. Tetrahedron: Asymmetry 1997; 8: 23
6h Hirt UH, Spingler B, Wirth T. J. Org. Chem. 1998; 63: 7674
6i Tohma H, Takizawa S, Watanabe H, Kita Y. Tetrahedron Lett. 1998; 39: 4547
6j Ochiai M, Kitagawa Y, Takayama N, Takaoka Y, Shiro M. J. Am. Chem. Soc. 1999; 121: 9233
6k Tohma H, Takizawa S, Watanabe H, Fukuoka Y, Maegawa T, Kita Y. J. Org. Chem. 1999; 64: 3519
6l Tohma H, Takizawa S, Morioka H, Maegawa T, Kita Y. Chem. Pharm. Bull. 2000; 48: 445
6m Hirt UH, Schuster MF. H, French AN, Wiest OG, Wirth T. Eur. J. Org. Chem. 2001; 1569
6n Altermann SM, Richardson RD, Page TK, Schmidt RK, Holland E, Mohammed U, Paradine SM, French AN, Richter C, Bahar AM, Witulski B, Wirth T. Eur. J. Org. Chem. 2008; 5315
6o Fujita M, Wakita M, Sugimura T. Chem. Commun. 2011; 47: 3983
6p Fujita M, Mori K, Shimogaki M, Sugimura T. Org. Lett. 2012; 14: 1294
6q Farid U, Wirth T. Angew. Chem. Int. Ed. 2012; 51: 3462
6r Farid U, Malmedy F, Claveau R, Albers L, Wirth T. Angew. Chem. Int. Ed. 2013; 52: 7018
6s Takesue T, Fujita M, Sugimura T, Akutsu H. Org. Lett. 2014; 16: 4634

7a Lebée C, Kataja AO, Blanchard F, Masson G. Chem. Eur. J. 2015; 21: 8399
7b Dumoulin A, Lalli C, Retailleau P, Masson G. Chem. Commun. 2015; 51: 5383
7c Lalli C, Dumoulin A, Lebée C, Drouet F, Guérineau V, Touboul D, Gandon V, Zhu J, Masson G. Chem. Eur. J. 2015; 21: 1704
7d Dagousset G, Erb W, Zhu J, Masson G. Org. Lett. 2014; 16: 2554
7e He L, Laurent G, Retailleau P, Folléas B, Brayer J.-L, Masson G. Angew. Chem. Int. Ed. 2013; 52: 11088
7f Courant T, Kumarn S, He L, Retailleau P, Masson G. Adv. Synth. Catal. 2013; 355: 836
7g He L, Bekkaye M, Retailleau P, Masson G. Org. Lett. 2012; 14: 3158
7h Dagousset G, Zhu J, Masson G. J. Am. Chem. Soc. 2011; 133: 14804
7i Liu H, Dagousset G, Masson G, Retailleau P, Zhu J. J. Am. Chem. Soc. 2009; 131: 4598

8a Carboni A, Dagousset G, Magnier E, Masson G. Org. Lett. 2014; 16: 1240
8b Bekkaye M, Su Y, Masson G. Eur. J. Org. Chem. 2013; 3978
8c Drouet F, Masson G, Zhu J. Org. Lett. 2013; 15: 2854
8d Drouet F, Fontaine P, Masson G, Zhu J. Synthesis 2009; 1370
8e Fontaine P, Chiaroni A, Masson G, Zhu J. Org. Lett. 2008; 10: 1509

9 Richardson RD, Page TK, Altermann S, Paradine SM, French AN, Wirth T. Synlett 2007; 538

10a Quideau S, Lyvinec G, Marguerit M, Bathany K, Ozanne-Beaudenon A, Buffeteau T, Cavagnat D, Chénedé A. Angew. Chem. Int. Ed. 2009; 48: 4605
10b Bosset C, Coffinier R, Peixoto PA, El Assal M, Miqueu K, Sotiropoulos J.-M, Pouységu L, Quideau S. Angew. Chem. Int. Ed. 2014; 53: 9860

11 Recently Wirth and co-workers reported the synthesis of chiral diaryliodonium salts derived from BINI, see: Brown M, Delorme M, Malmedy F, Malmgren J, Olofsson B, Wirth T. Synlett 2015; 26: 1573

12a Li T, Tsuda Y, Minoura K, In Y, Ishida T, Lazarus LH, Okada Y. Chem. Pharm. Bull. 2006; 54: 873
12b Miles KC, Le C, Stambuli JP. Chem. Eur. J. 2014; 20: 11336
12c Liu T.-F, Zou L, Feng D, Chen Y.-P, Fordham S, Wang X, Liu Y, Zhou H.-C. J. Am. Chem. Soc. 2014; 136: 7813

13a Guo H, Ding K. Tetrahedron Lett. 2000; 41: 10061
13b Kano T, Tanaka Y, Osawa K, Yurino T, Maruoka K. J. Org. Chem. 2008; 73: 7387

14 Also, see: Wang Y.-M, Kuzniewski CN, Rauniyar V, Hoong C, Toste FD. J. Am. Chem. Soc. 2011; 133: 12972

15a Kranz M, Clark T, vRSchleyer P. J. Org. Chem. 1993; 58: 3317
15b Brath H, Dubovská M, Juríček M, Kasák P, Putala M. Collect. Czech. Chem. Commun. 2004; 69: 1517
15c Brown KJ, Berry MS, Waterman KC, Lingenfelter D, Murdoch JR. J. Am. Chem. Soc. 1984; 106: 4717
15d Mešková M, Putala M. Tetrahedron Lett. 2011; 52: 5379
15e Kasak P, Brath H, Krascsenicsová-Polaková K, Kicková A, Moldovan N, Putala M. Collect. Czech. Chem. Commun. 2007; 72: 1139

16 Usanov DL, Yamamoto H. Angew. Chem. Int. Ed. 2010; 49: 8169
17 We obtained a mixture of non-reacted and over-acylated materials as major products. See also: Wang C.-J, Shi M. Eur. J. Org. Chem. 2003; 2823

18a Tohma H, Maruyama A, Maeda A, Maegawa T, Dohi T, Shiro M, Morita T, Kita Y. Angew. Chem. Int. Ed. 2004; 43: 3595
18b Dohi T, Maruyama A, Yoshimura M, Morimoto K, Tohma H, Shiro M, Kita Y. Chem. Commun. 2005; 2205

19a Lewis N, Wallbank P. Synthesis 1987; 1103
19b Barret R, Daudon M. Tetrahedron Lett. 1990; 31: 4871
19c Mal D, Roy HN, Hazra NK, Adhikari S. Tetrahedron 1997; 53: 2177
19d Quideau S, Looney MA, Pouységu L. Org. Lett. 1999; 1: 1651
19e Quideau S, Pouységu L, Oxoby M, Looney MA. Tetrahedron 2001; 57: 319
19f Wood JL, Graeber JK, Njardarson JT. Tetrahedron 2003; 59: 8855

20 Koser GF. Hypervalent Halogen Compounds . In The Chemistry of Functional Groups . Supplement D; Patai S, Rappoport Z. Wiley; Chichester: 1983: Chap. 18, 729

21a Lee C.-K, Mak TC. W, Li W.-K, Kirner JF. Acta Crystallogr., Sect. B 1977; 33: 1620
21b Alcock NW, Countryman RM, Esperás S, Sawyer JF. J. Chem. Soc., Dalton. Trans. 1979; 854

22a Siebert H, Handrich M. Z. Anorg. Allg. Chem. 1976; 426: 173
22b Gallos J, Varvoglis A, Alcock NW. J. Chem. Soc., Perkin Trans. 1 1985; 757

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