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Original Articles

Facile synthesis of bisphosphine monoxides from Morita–Baylis–Hillman carbonates

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Pages 885-890 | Received 06 Aug 2015, Accepted 22 Sep 2015, Published online: 27 Apr 2016

References

  • (a)Berners-Price, S. J.; Norman, R. E.; Sadler, P. J. J. Inorg. Biochem. 1987, 31, 197–209; (b)Debnath, A. K.; Radigan, L.; Jiang, S. J. Med. Chem. 1999, 42, 3203–3209.
  • Grushin, V. V. Chem. Rev. 2004, 104, 1629–1662 and references cited therein.
  • (a)Bader, A.; Lindner, E. Coord. Chem. Rev. 1991, 108, 27–110; (b)Slone, C. S.; Weinberger, D. A.; Mirkin, C. A. Prog. Inorg. Chem. 1999, 48, 233–350; (c)Braunstein, P.; Naud, F. Angew. Chem., Int. Ed. 2001, 40, 680–699.
  • (a)Farrer, N. J.; Mcdonald, R.; Piga, T.; McIndoe, J. S. Polyhedron. 2010, 29, 254–261; (b)Sues, P. E.; Lough, A. J.; Morris, R. H. Inorg. Chem. 2012, 51, 9322–9332; (c)Cyr, P. W.; Rettig, S. J.; Patrick, B. O.; James, B. R. Organometallics. 2002, 21, 4672–4679; (d)Oberhauser, W.; Manca, G.; Ienco, A.; Strabler, C.; Prock, J.; Weninger, A.; Gutmann, R.; Brüggeller, P. Organometallics. 2014, 33, 4067–4075; (e)Contrella, N. D.; Jordan, R. F. Organometallics. 2014, 33, 7199–7208.
  • (a)Abu-Gnim, C.; Amer, I. J. Organomet. Chem. 1996, 516, 235–243; (b)Ellis, D. D.; Harrison, G.; Orpen, A. G.; Phetmung, H.; Pringle, P. G.; deVries, J. G.; Oevering, H. J. Chem. Soc. Dalton Trans. 2000, 5, 671–675; (c)Weber, R.; Englert, U.; Ganter, B.; Keim, W.; Möhrath, M. Chem. Commun. 2000, 15, 1419–1420; (d)Roch-Neirey, C.; Le Bris, N.; Laurent, P.; Clément, J.-C.; des Abbayes, H. Tetrahedron Lett. 2001, 42, 643–645.
  • (a)Boezio, A. A.; Pytkowicz, J.; Côté, A.; Charette, A. B. J. Am. Chem. Soc. 2003, 125, 14260–14261; (b)Côté, A.; Boezio, A. A.; Charette, A. B. Proc. Natl. Acad. Sci. USA. 2004, 101, 5405–5410; (c)Desrosiers, J.-N.; Côté, A.; Charette, A. B. Tetrahedron. 2005, 61, 6186–6192; (d)Charette, A. B.; Boezio, A. A.; Côté, A.; Moreau, E.; Pytkowicz, J.; Desrosiers, J.-N.; Legault, C. Pure Appl. Chem. 2005, 77, 1259–1267; (e)Desrosiers, J.-N.; Côté, A.; Boezio, A. A.; Charette, A. B. Org. Synth. 2006, 83, 5; (f)Desrosiers, J.-N.; Charette, A. B. Angew. Chem. Int. Ed. 2007, 46, 5955; (g)Côté, A.; Lindsay, V. N. G.; Charette, A. B. Org. Lett. 2007, 9, 85–87; (h)Fukuzaki, Y.; Tomita, Y.; Terashima, T.; Ouchi, M.; Sawamoto, M. Macromolecules 2010, 43, 5989–5995; (i)Carrow, B. P; Nozaki, K. J. Am. Chem. Soc. 2012, 134, 8802–8805; (j)Boyd, D. R.; Bell, M.; Dunne, K. S.; Kelly, B.; Stevenson, P. J.; Malone, J. F.; Allen, C. C. R. Org. Biomol. Chem. 2012, 10, 1388–1395.
  • Xie, P.; Huang, Y. Org. Bimol. Chem. 2015, 13, 8578–8595.
  • For selected examples of [3 + n] annulations, see:(a)Du, Y.; Lu, X.; Zhang, C. Angew. Chem., Int. Ed. 2003, 42, 1035–1037; (b)Du, Y.; Feng, J.; Lu, X. Org. Lett. 2005, 7, 1987–1989; (c)Feng, J.; Lu, X.; Kong, A.; Han, X. Tetrahedron. 2007, 63, 6035–6041; (d)Zheng, S.; Lu, X. Org. Lett. 2008, 10, 4481; (e)Zheng, S.; Lu, X. Tetrahedron Lett. 2009, 50, 4532–4535; (f)Zheng, S.; Lu, X. Org. Lett. 2009, 11, 3978–3981; (g)Ye, L.-W.; Sun, X.-L.; Wang, Q.-G.; Tang, Y. Angew. Chem., Int. Ed. 2007, 46, 5951–5954; (h)Zhou, R.; Wang, J.; Song, H.; He, Z. Org. Lett. 2011, 13, 580–583; (i)Deng, H.-P.; Wei, Y.; Shi, M. Org. Lett. 2011, 13, 3348–3351; (j)Tan, B.; Candeias, N. R.; Barbas III, C. F. J. Am. Chem. Soc. 2011, 133, 4672–4675; (k)Zhong, F.; Han, X.; Wang, Y.; Lu, Y. Angew. Chem. Int. Ed. 2011, 50, 7837–7841. For examples of [1 + 4] annulations, see: (l)Chen, Z.; Zhang, J. Chem.-Asian J. 2010, 5, 1542–1545; (m)Xie, P.; Huang, Y.; Chen, R. Org. Lett. 2010, 12, 3768–3771; (n)Tian, J.; Zhou, R.; Sun, H.; Song, H.; He, Z. J. Org. Chem. 2011, 76, 2374–2378; (o)Zhang, X.-N.; Deng, H.-P.; Huang, L.; Wei, Y.; Shi, M. Chem. Commun. 2012, 48, 8664–8666; (p)Zhou, R.; Duan, C.; Yang, C.; He, Z. Chem.-Asian J. 2014, 9, 1183–1189.
  • For selected examples of phosphine-catalyzed allylic alkylations, see: (a)Cho, C.-W.; Kong, J.-R.; Krische, M. J. Org. Lett. 2004, 6, 1337–1339; (b)Cho, C. -W.; Krische, M. J. Angew. Chem. Int. Ed. 2004, 43, 6689–6691; (c)Park, H.; Cho, C.-W.; Krische, M. J. J. Org. Chem. 2006, 71, 7892–7894; (d)Jiang, Y.-Q.; Shi, Y.-L.; Shi, M. J. Am. Chem. Soc. 2008, 130, 7202–7203. For selected examples of teriary amine-catalyzed allylic alkylations, see: Du, Y.; Han, X.; Lu, X. Tetrahedron Lett. 2004, 45, 4967–4971; (f)Cui, H. L.; Feng, X.; Peng, J.; Lei, J.; Jiang, K.; Chen, Y. -C. Angew. Chem. Int. Ed. 2009, 48, 5737–5740; (g)Zhang, S. J.; Cui, H. L.; Jiang, K.; Li, R.; Ding, Z. Y.; Chen, Y.-C. Eur. J. Org. Chem. 2009, 5804–5809; (h)Cui, H. L.; Peng, J.; Feng, X.; Du, W.; Jiang, K.; Chen, Y.-C. Chem. Eur. J. 2009, 15, 1574–1577; (i)Cui, H. L.; Huang, J. R.; Lei, J.; Wang, Z. F.; Chen, S.; Wu, L.; Chen, Y.-C. Org. Lett. 2010, 12, 720–723.
  • Zhou, R.; Wang, J.; Duan, C.; He, Z. Org. Lett. 2012, 14, 6134–6137.
  • For recent examples, see: (a)Wang, Y.; Gan, J.; Liu, L.; Yuan, H.; Gao, Y.; Liu, Y.; Zhao, Y. J. Org. Chem. 2014, 79, 3678–3683; (b)Wu, Y.; Liu, L.; Yan, K.; Xu, P.; Gao, Y.; Zhao, Y. J. Org. Chem. 2014, 79, 8118–8127; (c)Liu, L.; Wu, Y.; Wang, Z.; Zhu, J.; Zhao, Y. J. Org. Chem. 2014, 79, 6816–6822; (d)Liu, L.; Lv, Y.; Wu, Y.; Gao, X.; Zeng, Z.; Gao, Y.; Tang, G.; Zhao, Y. RSC Adv. 2014, 4, 2322–2326; (e)Zhang, J. -S.; Chen, T.; Yang, J.; Han, L.-B. Chem. Commun. 2015, 51, 7540–7542; (f)Yang, J.; Chen, T.; Han, L. -B. J. Am. Chem. Soc. 2015, 137, 1782–1785.
  • (a)Barthélémy, S.; Schneider, S.; Bannwarth, W. Tetrahedron Lett. 2002, 43, 807–810; (b)Liu, L.; Wang, Y.; Zeng, Z.; Xu, P.; Gao, Y.; Yin, Y.; Zhao, Y. Adv. Synth. Catal. 2013, 355, 659–666.
  • Zhou, R.; Wang, C.; Song, H.; He, Z. Org. Lett. 2010, 12, 976–979 and references cited therein.
  • Mrabet, H.; Zantour, H. Phosphorus Sulfur Silicon Relat. Elem. 2004, 179, 25–33.

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