Synthesis 2012; 44(11): 1603-1613
DOI: 10.1055/s-0031-1289758
feature article
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Chromanes through RCM–Transfer Hydrogenation

Bernd Schmidt*
Universitaet Potsdam, Institut fuer Chemie (Organische Synthesechemie), Karl-Liebknecht-Straße 24-25, 14476 Potsdam-Golm, Germany, Fax: +49(331)9775059   Email: bernd.schmidt@uni-potsdam.de
,
Stefan Krehl
Universitaet Potsdam, Institut fuer Chemie (Organische Synthesechemie), Karl-Liebknecht-Straße 24-25, 14476 Potsdam-Golm, Germany, Fax: +49(331)9775059   Email: bernd.schmidt@uni-potsdam.de
,
Veronica Sotelo-Meza
Universitaet Potsdam, Institut fuer Chemie (Organische Synthesechemie), Karl-Liebknecht-Straße 24-25, 14476 Potsdam-Golm, Germany, Fax: +49(331)9775059   Email: bernd.schmidt@uni-potsdam.de
› Author Affiliations
Further Information

Publication History

Received: 02 March 2012

Received after revision: 23 March 2012

Publication Date:
24 April 2012 (online)


Abstract

A sequential ruthenium-catalyzed ring-closing metathesis–transfer hydrogenation sequence has been established as a synthesis of chromanes starting from 2-(allyloxy)styrenes. The sequence requires only one precatalyst, the first-generation Grubbs catalyst, which is converted into a ruthenium hydride species in situ. Propan-2-ol serves as a chemical trigger for the formation of the ruthenium hydride and as hydrogen source.

Supporting Information

 
  • References

  • 1 Alcaide B, Almendros P. Chem.–Eur. J. 2003; 9: 1259
  • 2 Schmidt B. Eur. J. Org. Chem. 2004; 1865
  • 3 Arisawa M, Terada Y, Takahashi K, Nakagawa M, Nishida A. Chem. Rec. 2007; 7: 238
  • 4 Alcaide B, Almendros P, Luna A. Chem. Rev. 2009; 109: 3817
  • 5 Chapman CJ, Frost CG. Synthesis 2007; 1
  • 6 Ambrosini LM, Lambert TH. ChemCatChem 2010; 2: 1373
  • 7 Fogg DE, dos Santos EN. Coord. Chem. Rev. 2004; 248: 2365
  • 8 Handbook of Metathesis . Grubbs RH. Wiley-VCH; Weinheim: 2003
  • 9 Schmidt B. Pure Appl. Chem. 2006; 78: 469
  • 10 Schmidt B, Pohler M. J. Organomet. Chem. 2005; 690: 5552
  • 11 Seigal BA, Fajardo C, Snapper ML. J. Am. Chem. Soc. 2005; 127: 16329
  • 12 Finnegan DF, Snapper ML. J. Org. Chem. 2011; 76: 3644
  • 13 Plietker B, Niggemann M. Org. Biomol. Chem. 2004; 2: 2403
  • 14 Plietker B. J. Org. Chem. 2004; 69: 8287
  • 15 Beligny S, Eibauer S, Maechling S, Blechert S. Angew. Chem. Int. Ed. 2006; 45: 1900
  • 16 Scholte AA, An MH, Snapper ML. Org. Lett. 2006; 8: 4759
  • 17 Neisius NM, Plietker B. J. Org. Chem. 2008; 73: 3218
  • 18 Peppers BP, Diver ST. J. Am. Chem. Soc. 2004; 126: 9524
  • 19 Kim BG, Snapper ML. J. Am. Chem. Soc. 2006; 128: 52
  • 20 Schmidt B, Krehl S. Chem. Commun. 2011; 47: 5879
  • 21 Kato H, Ishigame T, Oshima N, Hoshiya N, Shimawaki K, Arisawa M, Shuto S. Adv. Synth. Catal. 2011; 353: 2676
  • 22 Schrock RR, Murdzek JS, Bazan GC, Robbins J, DiMare M, O’Regan M. J. Am. Chem. Soc. 1990; 112: 3875
  • 23 Scholl M, Ding S, Lee CW, Grubbs RH. Org. Lett. 1999; 1: 953
  • 24 Schmidt B, Geißler D. ChemCatChem 2010; 2: 423
  • 25 Louie J, Bielawski CW, Grubbs RH. J. Am. Chem. Soc. 2001; 123: 11312
  • 26 Børsting P, Nielsen P. Chem. Commun. 2002; 2140
  • 27 Fürstner A, Leitner A. Angew. Chem. Int. Ed. 2003; 42: 308
  • 28 Schmidt B, Pohler M. Org. Biomol. Chem. 2003; 1: 2512
  • 29 Menozzi C, Dalko PI, Cossy J. Synlett 2005; 2449
  • 30 Sutton AE, Seigal BA, Finnegan DF, Snapper ML. J. Am. Chem. Soc. 2002; 124: 13390
  • 31 Schmidt B. Eur. J. Org. Chem. 2003; 816
  • 32 Schmidt B. Chem. Commun. 2004; 742
  • 33 Schmidt B. J. Org. Chem. 2004; 69: 7672
  • 34 van Otterlo WA. L, Coyanis EM, Panayides J.-L, de Koning CB, Fernandes MA. Synlett 2005; 501
  • 35 Drouin SD, Yap GP. A, Fogg DE. Inorg. Chem. 2000; 39: 5412
  • 36 Drouin SD, Zamanian F, Fogg DE. Organometallics 2001; 20: 5495
  • 37 Dinger MB, Mol JC. Organometallics 2003; 22: 1089
  • 38 Dinger MB, Mol JC. Eur. J. Inorg. Chem. 2003; 2827
  • 39 Banti D, Mol JC. J. Organomet. Chem. 2004; 689: 3113
  • 40 Louie J, Grubbs RH. Organometallics 2002; 21: 2153
  • 41 Arisawa M, Terada Y, Nakagawa M, Nishida A. Angew. Chem. Int. Ed. 2002; 41: 4732
  • 42 Schmidt B. Synlett 2004; 1541
  • 43 Schmidt B, Hölter F. Chem.–Eur. J. 2009; 15: 11948
  • 44 Schmidt B, Berger R, Hölter F. Org. Biomol. Chem. 2010; 8: 1406
  • 45 Schmidt B, Hölter F, Kelling A, Schilde U. J. Org. Chem. 2011; 76: 3357
  • 46 Schmidt B, Biernat A. Synlett 2007; 2375
  • 47 Schmidt B, Biernat A. Org. Lett. 2008; 10: 105
  • 48 Schmidt B, Biernat A. Chem.–Eur. J. 2008; 14: 6135
  • 49 Schmidt B. Chem. Commun. 2003; 1656
  • 50 Schmidt B, Biernat A. Eur. J. Org. Chem. 2008; 5764
  • 51 Schmidt B, Geißler D. Eur. J. Org. Chem. 2011; 4814
  • 52 Schmidt B, Staude L. J. Organomet. Chem. 2006; 691: 5218
  • 53 Cho CS, Kim BT, Kim H.-S, Kim T.-J, Shim SC. Organometallics 2003; 22: 3608
  • 54 Burling S, Whittlesey MK, Williams JM. J. Adv. Synth. Catal. 2005; 347: 591
  • 55 Nixon TD, Whittlesey MK, Williams JM. J. Dalton Trans. 2009; 753
  • 56 van Otterlo WA. L, Ngidi EL, Coyanis EM, de Koning CB. Tetrahedron Lett. 2003; 44: 311
  • 57 van Otterlo WA. L, Ngidi EL, Kuzvidza S, Morgans GL, Moleele SS, de Koning CB. Tetrahedron 2005; 61: 9996
  • 58 Machado AH. L, de Sousa MA, Patto DC. S, Azevedo LF. S, Bombonato FI, Correia CR. D. Tetrahedron Lett. 2009; 50: 1222
  • 59 Demyttenaere J, Van Syngel K, Markusse AP, Vervisch S, Debenedetti S, De Kimpe N. Tetrahedron 2002; 58: 2163
  • 60 Chang S, Grubbs RH. J. Org. Chem. 1998; 63: 864
  • 61 Kleemann A, Engel J, Kutscher B, Reichert D. Pharmaceutical Substances . 5th ed. Georg Thieme Verlag; Stuttgart: 2009
  • 62 Doi F, Ohara T, Ogamino T, Sugai T, Higashinakasu K, Yamada K, Shigemori H, Hasegawa K, Nishiyama S. Phytochemistry 2004; 65: 1405
  • 63 Doi F, Ohara T, Ogamino T, Higashinakasu K, Hasegawa K, Nishiyama S. Bull. Chem. Soc. Jpn. 2004; 77: 2257
  • 64 Rial E, Rodríguez-Sánchez L, Aller P, Guisado A, Mar González-Barroso M, Gallardo-Vara E, Redondo-Horcajo M, Castellanos E, Fernández de la Pradilla R, Viso A. Chem. Biol. 2011; 18: 264
  • 65 Xie K, Wang S, Li P, Li X, Yang Z, An X, Guo C.-C, Tan Z. Tetrahedron Lett. 2010; 51: 4466
  • 66 Polito L, Cravini M, Poletti L, Lay L. Synth. Commun. 2006; 36: 2203
  • 67 Hayashi T, Matsumoto Y, Ito Y. Tetrahedron: Asymmetry 1991; 2: 601
  • 68 Nettekoven U, Hartwig JF. J. Am. Chem. Soc. 2002; 124: 1166
  • 69 Doucet H, Fernandez E, Layzell TP, Brown JM. Chem.–Eur. J. 1999; 5: 1320
  • 70 Schwab P, Grubbs RH, Ziller JW. J. Am. Chem. Soc. 1996; 118: 100
  • 71 Niu J, Guo P, Kang J, Li Z, Xu J, Hu S. J. Org. Chem. 2009; 74: 5075
  • 72 Hanamoto T, Shindo K, Matsuoka M, Kiguchi Y, Kondo M. J. Chem. Soc., Perkin Trans. 1 2000; 103
  • 73 Hong DJ, Kim DW, Chi DY. Tetrahedron Lett. 2010; 51: 54
  • 74 Huang K.-S, Li S.-R, Wang Y.-F, Lin Y.-L, Chen Y.-H, Tsai T.-W, Yang C.-H, Wang E.-C. J. Chin. Chem. Soc. 2005; 52: 159
  • 75 Elias X, Pleixats R, Wong Chi Man M. Tetrahedron 2008; 64: 6770