Ring-Expansion Reactions of Binaphthyl Azepines and Ferrocenophanes through Metal-Catalyzed [1,2]-Stevens Rearrangements

Steven Harthong; Renaud Bach; Céline Besnard; Laure Guénée; Jérôme Lacour

doi:10.1055/s-0033-1339188

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(15): 2070-2078
DOI: 10.1055/s-0033-1339188

feature article

Ring-Expansion Reactions of Binaphthyl Azepines and Ferrocenophanes through Metal-Catalyzed [1,2]-Stevens Rearrangements

Steven Harthong

^aUniversity of Geneva, Department of Organic Chemistry, Quai Ernest Ansermet 30, 1211 Geneva 4, Switzerland Fax: +41(22)3793215 eMail: jerome.lacour@unige.ch

,

Renaud Bach

^aUniversity of Geneva, Department of Organic Chemistry, Quai Ernest Ansermet 30, 1211 Geneva 4, Switzerland Fax: +41(22)3793215 eMail: jerome.lacour@unige.ch

,

Céline Besnard

^bUniversity of Geneva, Laboratory of Crystallography, Quai Ernest Ansermet 24, 1211 Geneva 4, Switzerland

,

Laure Guénée

^bUniversity of Geneva, Laboratory of Crystallography, Quai Ernest Ansermet 24, 1211 Geneva 4, Switzerland

,

Jérôme Lacour*

^aUniversity of Geneva, Department of Organic Chemistry, Quai Ernest Ansermet 30, 1211 Geneva 4, Switzerland Fax: +41(22)3793215 eMail: jerome.lacour@unige.ch

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Abstract

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Abstract

Enantiopure binaphthyl azocines can be prepared in a single step via the direct copper-catalyzed reaction of binaphthyl azepines and α-diazo carbonyl reagents. The [1,2]-Stevens rearrangement is general (61–93% yields) and can be extended to [3]ferrocenophanes; similar reactivity in favor of the products of ring expansion is obtained with these ferrocene derivatives (80–96% yields).

Key words

azepine - azocine - diazo ester - ferrocenophane - [1,2]-Stevens rearrangement

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Referenzen

References
1 Ikunaka M, Maruoka K, Okuda Y, Ooi T. Org. Process Res. Dev. 2003; 7: 644

2a Arimitsu S, Kato D, Maruoka K. Chem. Lett. 2011; 40: 1115
2b Gembus V, Postikova S, Levacher V, Briere J.-F. J. Org. Chem. 2011; 76: 4194
2c Hashimoto T, Sakata K, Maruoka K. Angew. Chem. Int. Ed. 2009; 48: 5014
2d Hashimoto T, Sasaki K, Fukumoto K, Murase Y, Abe N, Ooi T, Maruoka K. Chem. Asian J. 2010; 5: 562
2e He R, Shirakawa S, Maruoka K. J. Am. Chem. Soc. 2009; 131: 16620
2f Hua M.-Q, Cui H.-F, Wang L, Nie J, Ma J.-A. Angew. Chem. Int. Ed. 2010; 49: 2772
2g Hua M.-Q, Wang L, Cui H.-F, Nie J, Zhang X.-L, Ma J.-A. Chem. Commun. 2011; 47: 1631
2h Kano T, Yamamoto A, Song S, Maruoka K. Chem. Commun. 2011; 47: 4358
2i Lan Q, Wang X, Shirakawa S, Maruoka K. Org. Process Res. Dev. 2010; 14: 684
2j Nie J, Hua M.-Q, Xiong H.-Y, Zheng Y, Ma J.-A. J. Org. Chem. 2012; 77: 4209
2k Park Y, Kang S, Lee YJ, Kim T.-S, Jeong B.-S, Park H.-g, Jew S.-s. Org. Lett. 2009; 11: 3738
2l Park Y, Lee YJ, Hong S, Kim M.-h, Lee M, Kim T.-S, Lee JK, Jew S.-s, Park H.-g. Adv. Synth. Catal. 2011; 353: 3313
2m Shirakawa S, Liu K, Ito H, Maruoka K. Chem. Commun. 2011; 47: 1515
2n Shirakawa S, Liu K, Maruoka K. J. Am. Chem. Soc. 2012; 134: 916
2o Shirakawa S, Ota K, Terao SJ, Maruoka K. Org. Biomol. Chem. 2012; 10: 5753
2p Shirakawa S, Terao SJ, He R, Maruoka K. Chem. Commun. 2011; 47: 10557
2q Wang L, Shirakawa S, Maruoka K. Angew. Chem. Int. Ed. 2011; 50: 5327
2r Wang X, Kitamura M, Maruoka K. J. Am. Chem. Soc. 2007; 129: 1038
2s Wang X, Lan Q, Shirakawa S, Maruoka K. Chem. Commun. 2010; 46: 321

3 Jung SH, Kim DY. Tetrahedron Lett. 2008; 49: 5527

4a Aggarwal VK, Wang MF. Chem. Commun. 1996; 191
4b Bulman Page PC, Bartlett CJ, Chan Y, Day D, Parker P, Buckley BR, Rassias GA, Slawin AM. Z, Allin SM, Lacour J, Pinto A. J. Org. Chem. 2012; 77: 6128
4c Goncalves M.-H, Martinez A, Grass S, Bulman Page PC, Lacour J. Tetrahedron Lett. 2006; 47: 5297
4d Novikov R, Bernardinelli G, Lacour J. Adv. Synth. Catal. 2008; 350: 1113
4e Novikov R, Bernardinelli G, Lacour J. Adv. Synth. Catal. 2009; 351: 596
4f Novikov R, Lacour J. Tetrahedron: Asymmetry 2010; 21: 1611
4g Bulman Page PC, Farah MM, Buckley BR, Blacker AJ, Lacour J. Synlett 2008; 1381

5 Vachon J, Lauper C, Ditrich K, Lacour J. Tetrahedron: Asymmetry 2006; 17: 2334
6 Superchi S, Mecca T, Giorgio E, Rosini C. Tetrahedron: Asymmetry 2001; 12: 1235

7a Wimmer P, Widhalm M. Tetrahedron: Asymmetry 1995; 6: 657
7b Zalubovskis R, Bouet A, Fjellander E, Constant S, Linder D, Fischer A, Lacour J, Privalov T, Moberg C. J. Am. Chem. Soc. 2008; 130: 1845

8a Stara IG, Stary I, Tichy M, Zavada J, Fiedler P. J. Org. Chem. 1994; 59: 1326
8b Stara IG, Stary I, Tichy M, Zavada J, Hanus V. J. Am. Chem. Soc. 1994; 116: 5084

9a Bach R, Harthong S, Lacour J. Nitrogen- and Sulfur-Based Stevens and Related Rearrangements. In Comprehensive Organic Synthesis II. Molander G, Knochel P. Elsevier; London: 2014. volume in press
9b Markó IE. The Stevens and Related Rearrangements. In Comprehensive Organic Synthesis. Vol. 3. Trost BM, Fleming I. Pergamon Press; Oxford: 1991: 913
9c Vanecko JA, Wan H, West FG. Tetrahedron 2006; 62: 1043

10 Goncalves-Farbos MH, Vial L, Lacour J. Chem. Commun. 2008; 829

11a Ariza M, Díaz A, Suau R, Valpuesta M. Eur. J. Org. Chem. 2011; 6507
11b Beall LS, Padwa A. Tetrahedron Lett. 1998; 39: 4159
11c Bott TM, Vanecko JA, West FG. J. Org. Chem. 2009; 74: 2832
11d Brewster JH, Jones RS. J. Org. Chem. 1969; 34: 354
11e Chelucci G, Saba A, Valenti R, Bacchi A. Tetrahedron: Asymmetry 2000; 11: 3449
11f Couty F, Durrat F, Evano G, Prim D. Tetrahedron Lett. 2004; 45: 7525
11g Kitano T, Shirai N, Sato Y. Chem. Pharm. Bull. 1992; 40: 768
11h Michon C, Sharma A, Bernardinelli G, Francotte E, Lacour J. Chem. Commun. 2010; 46: 2206
11i Molchanov AP, Stepakov AV, Kopf J, Zenkevich IG, Kostikov RR. Russ. Chem. Bull., Int. Ed. 2001; 50: 2144
11j Mucedda M, Muroni D, Saba A, Manassero C. Tetrahedron 2007; 63: 12232
11k Muroni D, Saba A, Culeddu N. Tetrahedron: Asymmetry 2004; 15: 2609
11l Naidu BN, West FG. Tetrahedron 1997; 53: 16565
11m Padwa A, Beall LS, Eidell CK, Worsencroft KJ. J. Org. Chem. 2001; 66: 2414
11n Pedrosa R, Andres C, Delgado M. Synlett 2000; 893
11o Roberts E, Sancon JP, Sweeney JB. Org. Lett. 2005; 7: 2075
11p Saba A. Tetrahedron Lett. 2003; 44: 2895
11q Valpuesta M, Ariza M, Diaz A, Suau R. Eur. J. Org. Chem. 2010; 4393
11r Vanecko JA, West FG. Org. Lett. 2002; 4: 2813
11s Vanecko JA, West FG. Org. Lett. 2005; 7: 2949
11t West FG, Naidu BN. J. Am. Chem. Soc. 1994; 116: 8420

12a Sharma A, Besnard C, Guenee L, Lacour J. Org. Biomol. Chem. 2012; 10: 966
12b Sharma A, Guenee L, Naubron JV, Lacour J. Angew. Chem. Int. Ed. 2011; 50: 3677

13a Austeri M, Rix D, Zeghida W, Lacour J. Org. Lett. 2011; 13: 1394
13b Ballesteros-Garrido R, Rix D, Besnard C, Lacour J. Chem. Eur. J. 2012; 18: 6626
13c Rix D, Ballesteros-Garrido R, Zeghida W, Besnard C, Lacour J. Angew. Chem. Int. Ed. 2011; 50: 7308
13d Tortoreto C, Achard T, Zeghida W, Austeri M, Guénée L, Lacour J. Angew. Chem. Int. Ed. 2012; 51: 5847
13e Zeghida W, Besnard C, Lacour J. Angew. Chem. Int. Ed. 2010; 49: 7253

14 Cottineau F, Maigrot N, Mazaleyrat J.-P. Tetrahedron Lett. 1985; 26: 421
15 Ferrocenes: Ligands, Materials and Biomolecules. Stepnicka P. John Wiley; Chichester: 2008
16 Aggarwal VK, Jones D, Turner ML, Adams H. J. Organomet. Chem. 1996; 524: 263

17a Sakano T, Horie M, Osakada K, Nakao H. Bull. Chem. Soc. Jpn. 2001; 74: 2059
17b Yamaguchi I, Sakano T, Ishii H, Osakada K, Yamamoto T. J. Organomet. Chem. 1999; 584: 213

18 Carlstroem AS, Frejd T. J. Org. Chem. 1990; 55: 4175
19 The sum of the absolute values of the distortions from 120° at the N atoms are respectively 10.3° for both 8a and 9a, 8.7° for 10a and 3.75° for 11a.
20 The barrier was estimated using the equation (ΔG ^≠ = RT _c{22.96 + ln [Tc/√(Δν² + 6 J _AB ²)]} with ΔG ^≠ being the free energy of activation, T _c the temperature of coalescence, [ν the difference in frequency for the methylene peaks (140 Hz) and J _AB the coupling constant (16.5 Hz)].
21 Stará IG, Starý I, Závada J. Tetrahedron: Asymmetry 1992; 3: 1365

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