7-Siloxy-Substituted Hexahydronaphthalene Derivatives: Samarium Diiodide Promoted Synthesis and Typical Reactions

André Niermann; Hans-Ulrich Reissig

doi:10.1055/s-0040-1707889

Synthesis, Table of Contents

Synthesis 2020; 52(18): 2721-2730
DOI: 10.1055/s-0040-1707889

paper

7-Siloxy-Substituted Hexahydronaphthalene Derivatives: Samarium Diiodide Promoted Synthesis and Typical Reactions

André Niermann

,

Hans-Ulrich Reissig ∗

Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany Email: hans.reissig@chemie.fu-berlin.de

› Author Affiliations

Abstract

All articles of this category

Dedicated to Professor Helmut Vorbrüggen on the occasion of his 90^th birthday

Abstract

The samarium diiodide promoted reductive cyclization of a series of γ-aryl ketones with acetoxy, alkoxy, and siloxy groups in ortho-, meta-, and para-positions was investigated. Only precursors with p-acetoxy, p-tert-butoxy, or p-siloxy substituents furnished decent yields of the desired 7-oxy-1,2,3,4,6,8a-hexahydronaphthalene derivatives. The products were formed without contamination with the regioisomeric bicyclic products containing conjugated double bonds. Typical reactions exploiting the silyl enol ether moiety of the 7-(tert-butyldimethylsiloxy)-1,2,3,4,6,8a-hexahydronaphthalene derivative were performed, allowing stereoselective access to highly substituted hexahydro-, octahydro-, or decahydronaphthalene derivatives.

Key words

dearomatization - ketyl - hexahydronaphthalene - radical - samarium diiodide - silyl enol ether

Full Text

References

References

For general reviews dealing with synthetic applications of dearomatizing processes, see:

1a Mander LN. Synlett 1991; 134
1b Pape AR, Kaliappan KP, Kündig EP. Chem. Rev. 2000; 100: 2917
1c Ortiz FL, Iglesias MJ, Fernández I, Sánchez CM. A, Gómez GR. Chem. Rev. 2007; 107: 1580
1d Quideau S, Pouységu L, Deffieux D. Synlett 2008; 467
1e Zhuo C.-X, Zhang W, You S.-L. Angew. Chem. Int. Ed. 2012; 51: 12662 ; Angew. Chem. 2012, 124, 12834
1f Ding Q, Zhou X, Fan R. Org. Biomol. Chem. 2014; 12: 4807
1g Zhuo C.-X, Zheng C, You S.-L. Acc. Chem. Res. 2014; 47: 2558
1h Denizot N, Tomakinian T, Beaud R, Kouklovsky C, Vincent G. Tetrahedron Lett. 2015; 56: 4413
1i Wu T, Zhang L, You S.-L. Chem. Soc. Rev. 2016; 45: 1570
1j Okumura M, Sarlah D. Synlett 2018; 29: 845
1k Wertjes WC, Southgate EM, Sarlah D. Chem. Soc. Rev. 2018; 47: 7996
1l Zeidan M, Lautens M. Synthesis 2019; 51: 4137
1m Okumura M, Sarlah D. Eur. J. Org. Chem. 2020; 1259

For reviews concentrating on reductive dearomatization reactions, see:

2a Donohoe TJ, Garg R, Stevenson CA. Tetrahedron: Asymmetry 1996; 7: 317
2b Roche SP, Porco JA. Angew. Chem. Int. Ed. 2011; 50: 4068 ; Angew. Chem. 2011, 123, 4154

For the first publications, see:

3a Namy J.-L, Kagan HB. Nouv. J. Chim. 1977; 1: 5
3b Girard P, Namy J.-L, Kagan HB. J. Am. Chem. Soc. 1980; 102: 2693

For reviews, see:

3c Molander GA, Harris CR. Chem. Rev. 1996; 96: 307
3d Edmonds DJ, Johnston D, Procter DJ. Chem. Rev. 2004; 104: 3371
3e Gopalaiah K, Kagan HB. New J. Chem. 2008; 32: 607
3f Nicolaou KC, Ellery SP, Chen JS. Angew. Chem. Int. Ed. 2009; 48: 7140 ; Angew. Chem. 2009, 121, 7276
3g Procter DJ, Flowers RA. II, Skrydstrup T. Organic Synthesis Using Samarium Diiodide: A Practical Guide . Royal Society of Chemistry; Cambridge: 2010
3h Honda T. Heterocycles 2011; 83: 1
3i Szostak M, Procter DJ. Angew. Chem. Int. Ed. 2012; 51: 9238 ; Angew. Chem. 2012, 124, 9372
3j Gopalaiah K, Kagan HB. Chem. Rec. 2013; 13: 187
3k Szostak M, Spain M, Procter MJ. Chem. Soc. Rev. 2013; 42: 9155
3l Szostak M, Fazakerley NJ, Parmar D, Procter DJ. Chem. Rev. 2014; 114: 5959
3m Just-Baringo X, Procter DJ. Acc. Chem. Res. 2015; 48: 1263
3n Plesniak MP, Huang H.-M, Procter DJ. Nat. Rev. Chem. 2017; 1: 0077

For cyclizations of arenes leading to carbocyclic compounds, see:

4a Dinesh CU, Reissig H.-U. Angew. Chem. Int. Ed. 1999; 38: 789 ; Angew. Chem. 1999, 111, 874
4b Nandanan E, Dinesh CU, Reissig H.-U. Tetrahedron 2000; 56: 4267
4c Berndt M, Hlobilová I, Reissig H.-U. Org. Lett. 2004; 6: 957
4d Aulenta F, Berndt M, Brüdgam I, Hartl H, Sörgel S, Reissig H.-U. Chem. Eur. J. 2007; 13: 6047
4e Wefelscheid UK, Reissig H.-U. Adv. Synth. Catal. 2008; 350: 65
4f Wefelscheid UK, Reissig H.-U. Tetrahedron: Asymmetry 2010; 21: 1601
4g Niermann A, Reissig H.-U. Synlett 2011; 525

For selected references on cyclizations of (hetero)arenes leading to heterocyclic compounds, see:

5a Gross S, Reissig H.-U. Synlett 2002; 2027
5b Beemelmanns C, Blot V, Gross S, Lentz D, Reissig H.-U. Eur. J. Org. Chem. 2010; 2716
5c Beemelmanns C, Reissig H.-U. Angew. Chem. Int. Ed. 2010; 49: 8021 ; Angew. Chem. 2010, 122, 8195
5d Rao CN, Lentz D, Reissig H.-U. Angew. Chem. Int. Ed. 2015; 54: 2750 ; Angew. Chem. 2015, 127, 2788
5e Rao CN, Bentz C, Reissig H.-U. Chem. Eur. J. 2015; 21: 15951
5f Achazi AJ, Andrae D, Reissig H.-U, Paulus B. J. Comput. Chem. 2017; 38: 2693
5g Mao H, You B.-X, Zhou L.-J, Xie T.-T, Wen Y-H, Lv X, Wang X.-X. Org. Biomol. Chem. 2017; 15: 6157
5h Beemelmanns C, Bentz C, Nitsch D, Reissig H.-U. Chem. Eur. J. 2019; 21: 8780

For reviews summarizing our work, see:

6a Berndt M, Gross S, Hölemann A, Reissig H.-U. Synlett 2004; 422
6b Beemelmanns C, Reissig H.-U. Pure Appl. Chem. 2011; 83: 507
6c Beemelmanns C, Reissig H.-U. Chem. Soc. Rev. 2011; 40: 2199
6d Beemelmanns C, Reissig H.-U. Chem. Rec. 2015; 15: 872

For related samarium diiodide induced aryl couplings, see:

7a Schmalz H.-G, Siegel S, Bats JW. Angew. Chem. Int. Ed. 1995; 34: 2383 ; Angew. Chem. 1995, 107, 2597
7b Schmalz H.-G, Kiehl O, Gotov B. Synlett 2002; 1253
7c Shiue J.-S, Lin C.-C, Fang J.-M. J. Org. Chem. 1997; 62: 4643
7d Kuo C.-W, Fang J.-M. Synth. Commun. 2001; 31: 877
7e Huang H.-M, Procter DJ. J. Am. Chem. Soc. 2017; 139: 1661
7f Huang H.-M, McDouall JJ. W, Procter DJ. Nat. Catal. 2019; 2: 211

For electrochemical reductive cyclizations of related substrates, see:

7g Shono T, Kise N, Suzumoto T, Morimoto T. J. Am. Chem. Soc. 1986; 108: 4676
7h Kise N, Suzumoto T, Shono T. J. Org. Chem. 1994; 59: 1407
7i Gorny R, Schäfer HJ, Fröhlich R. Angew. Chem. Int. Ed. 1995; 34: 2007 ; Angew. Chem. 1995, 107, 2188
7j Heinemann J, Schäfer HJ, Fröhlich R, Wibbeling B. Eur. J. Org. Chem. 2003; 2919

HMPA strongly increases the reducing ability of samarium diiodide and is therefore used for many ketyl coupling reactions, see:

8a Inanaga J, Ishikawa M, Yamaguchi M. Chem. Lett. 1987; 1485
8b Prasad E, Flowers RA. II. J. Am. Chem. Soc. 2002; 124: 6895
8c Dahlén A, Hilmersson G. Eur. J. Inorg. Chem. 2004; 3393
8d Flowers RA. II. Synlett 2008; 1427
8e Halder S, Hoz S. J. Org. Chem. 2014; 79: 2682

Since HMPA is carcinogenic and teratogenic, related additives without these harmful effects have been studied. Tripyrrolidinophosphoric acid triamide (TPPA) can often serve as a good substitute, see:

9a McDonald CE, Ramsey JD, Sampsell DG, Butler JA, Cecchini MR. Org. Lett. 2010; 12: 5178
9b Berndt M, Hölemann A, Niermann A, Bentz C, Zimmer R, Reissig H.-U. Eur. J. Org. Chem. 2012; 1299
9c McDonald CE, Ramsey JD, Sampsell DG, Anderson LA, Krebs JE, Smith SN. Tetrahedron 2013; 69: 2947

For stereoelectronic effects in radical cyclizations, see:

10a Beckwith AL. J. Tetrahedron 1981; 37: 3073
10b Spellmeyer DC, Houk KN. J. Org. Chem. 1987; 52: 959

11a Berndt M, Reissig H.-U. Synlett 2001; 1290
11b Wefelscheid UK, Berndt M, Reissig H.-U. Eur. J. Org. Chem. 2008; 3635

For related studies of aryl ketones with electron-withdrawing substituents, see:

12a Ohno H, Maeda S, Okumura M, Wakayama R, Tanaka T. Chem. Commun. 2002; 316
12b Ohno H, Wakayama R, Maeda S, Iwasaki H, Okumura M, Iwata C, Mikamiyama H, Tanaka T. J. Org. Chem. 2003; 68: 5909
12c Ohno H, Okumura M, Maeda S, Iwasaki H, Wakayama R, Tanaka T. J. Org. Chem. 2003; 68: 7722
12d Ohno H, Iwasaki H, Eguchi T, Tanaka T. Chem. Commun. 2004; 2228
12e Iwasaki H, Eguchi T, Tsutsui N, Ohno H, Tanaka T. J. Org. Chem. 2008; 73: 7145
12f Iwasaki H, Tsutsui N, Eguchi T, Ohno H, Yamashita M, Tanaka T. Tetrahedron Lett. 2011; 52: 1770

13 For the cyclizations of (p-methoxyphenyl)pentan-2-one we obtained products of type F and G in ratios between 4:1 to 1:1 (together with aromatized compound I and reduced precursor H). So far it is not clear whether the protonation of the intermediate anion is kinetically controlled or whether a subsequent proton shift occurs. Even (partial) hydrogen abstraction from THF at an earlier stage of the multistep reaction is possible. See: Niermann A. Dissertation . Freie Universität Berlin; Germany: 2012

14a Tamaru Y, Ochiai H, Nakamura T, Tsubaki K, Yoshida Z. Tetrahedron Lett. 1985; 26: 5559
14b Tamaru Y, Ochiai H, Nakamura T, Yoshida Z. Tetrahedron Lett. 1986; 27: 955

15 Figadere B, Norman AW, Henry HL, Koeffler HP, Zhou JY, Okamura WH. J. Med. Chem. 1991; 34: 2452
16 Chiarello J, Joullié MM. Tetrahedron 1988; 44: 41
17 Mukaiyama T. Angew. Chem. Int. Ed. 1977; 16: 817; Angew. Chem. 1977, 89, 858

18a Mehta G, Sen S. Eur. J. Org. Chem. 2009; 123
18b Mehta G, Sen S, Kumara TH. S. Tetrahedron 2011; 3440
18c Mehta G, Sen S. Chimia 2012; 66: 892
18d Malik M, Jarosz S. Beilstein J. Org. Chem. 2016; 12: 2602
18e Hedberg C, Estrup M, Eikeland EZ, Jensen HH. J. Org. Chem. 2018; 83: 2154

19 Zimmer R, Reissig H.-U. J. Org. Chem. 1992; 57: 339
20 Reissig H.-U, Hippeli C, Arnold T. Chem. Ber. 1990; 123: 2403
21 Reissig H.-U, Zimmer R. Chem. Rev. 2003; 103: 1151

22a Reissig H.-U, Hirsch E. Angew. Chem. Int. Ed. 1980; 19: 813 ; Angew. Chem. 1980, 92, 839
22b Kunkel E, Reichelt I, Reissig H.-U. Liebigs Ann. Chem. 1984; 512

23 Kunkel E, Reichelt I, Reissig H.-U. Liebigs Ann. Chem. 1984; 802

Supplementary Material

Supporting Information