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Contents Vol 64(8)

N-Heterocyclic Carbene-Promoted Rauhut–Currier Reactions between Vinyl Sulfones and α,β-Unsaturated Aldehydes

Roxanne L. Atienza A and Karl A. Scheidt A B
+ Author Affiliations
- Author Affiliations

A Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Silverman Hall, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208, USA.

B Corresponding author. Email: scheidt@northwestern.edu

Australian Journal of Chemistry 64(8) 1158-1164 https://doi.org/10.1071/CH11264
Submitted: 8 July 2011  Accepted: 19 July 2011   Published: 19 August 2011

Abstract

N-heterocyclic carbenes (NHCs) promote the addition of 1,1-bis(phenylsulfonyl)ethylene to the α-position of α,β-unsaturated aldehydes. The proposed reaction pathway for this Rauhut–Currier-type reaction includes an unusual conjugate addition of an NHC to a bis-vinyl sulfone.


References

[1]  (a) P. Dalko, L. Moisan, Angew. Chem. Int. Ed. 2004, 43, 5138.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXos1Kmsr4%3D&md5=482247fc24aad012a2a3290ebde8377bCAS |
      (b) B. List, Chem. Commun. 2006, 8, 819.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) D. W. C. MacMillan, Nature 2008, 455, 304.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) S. Bertelsen, K. A. Jorgensen, Chem. Soc. Rev. 2009, 38, 2178.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) D. Kampen, C. M. Reisinger, B. List, Top. Curr. Chem. 2009, 291, 395.
         | Crossref | GoogleScholarGoogle Scholar |

[2]  S. E. Denmark, G. L. Beutner, Angew. Chem. Int. Ed. 2008, 47, 1560.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXis1Krtr8%3D&md5=43fff5756e28d1b8ebb115f4659fe70eCAS |

[3]  (a) D. Enders, T. Balensiefer, Acc. Chem. Res. 2004, 37, 534.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXisVequ7Y%3D&md5=db021f18ae8da812b6b9bc885ee084a2CAS |
      N-Heterocyclic Carbenes in Synthesis (Ed S. P. Nolan) 2006 (Wiley-VCH: Weinheim).
      (c) D. Enders, O. Niemeier, A. Henseler, Chem. Rev. 2007, 107, 5606.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) V. Nair, S. Vellalath, B. Babu, Chem. Soc. Rev. 2008, 37, 2691.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) E. M. Phillips, A. Chan, K. A. Scheidt, Aldrichim. Acta 2009, 42, 55.

[4]  (a) T. Ugai, S. Tanaka, S. Dokawa, J. Pharm. Soc. Jpn 1943, 63, 269.
      (b) R. Breslow, J. Am. Chem. Soc. 1958, 80, 3719.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) Y. Hachisu, J. W. Bode, K. Suzuki, J. Am. Chem. Soc. 2003, 125, 8432.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) A. Chan, K. A. Scheidt, J. Am. Chem. Soc. 2006, 128, 4558.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) D. Enders, K. Breuer, J. Runsink, J. H. Teles, Helv. Chim. Acta 1996, 79, 1899.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) D. Enders, K. Breuer, J. H. Teles, Helv. Chim. Acta 1996, 79, 1217.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) D. Enders, U. Kallfass, Angew. Chem. Int. Ed. 2002, 41, 1743.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) M. S. Kerr, J. R. de Alaniz, T. Rovis, J. Am. Chem. Soc. 2002, 124, 10298.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  (a) C. Burstein, F. Glorius, Angew. Chem. Int. Ed. 2004, 43, 6205.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhtVKnurbF&md5=160f1e1725bebed6d472257f537d1ff6CAS |
      (b) S. S. Sohn, E. L. Rosen, J. W. Bode, J. Am. Chem. Soc. 2004, 126, 14370.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) A. Chan, K. A. Scheidt, Org. Lett. 2005, 7, 905.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) V. Nair, S. Vellalath, M. Poonoth, E. Suresh, J. Am. Chem. Soc. 2006, 128, 8736.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) A. Chan, K. A. Scheidt, J. Am. Chem. Soc. 2007, 129, 5334.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) V. Nair, S. C. Mathew, A. T. Biju, E. Suresh, Angew. Chem. 2007, 119, 2116.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) A. Chan, K. A. Scheidt, J. Am. Chem. Soc. 2008, 130, 2740.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) E. M. Phillips, T. E. Reynolds, K. A. Scheidt, J. Am. Chem. Soc. 2008, 130, 2416. For NHC catalysis with.
         | Crossref | GoogleScholarGoogle Scholar |
      (i) B. Cardinal-David, D. E. A. Raup, K. A. Scheidt, J. Am. Chem. Soc. 2010, 132, 5345.
         | Crossref | GoogleScholarGoogle Scholar |
      (j) D. E. A. Raup, B. Cardinal-David, D. Holte, K. A. Scheidt, Nat. Chem. 2010, 2, 766.
         | Crossref | GoogleScholarGoogle Scholar |
      (k) D. Cohen, B. Cardinal-David, K. A. Scheidt, Angew. Chem. Int. Ed. 2011, 50, 1678.
         | Crossref | GoogleScholarGoogle Scholar |
      (l) D. Cohen, B. Cardinal-David, J. M. Roberts, A. A. Sarjeant, K. A. Scheidt, Org. Lett. 2011, 13, 1068.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  (a) K. Chow, J. W. Bode, J. Am. Chem. Soc. 2004, 126, 8126.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXkvVSjtLc%3D&md5=4ac98b0704d25566d856282ea151ddcfCAS |
      (b) N. Reynolds, T. Rovis, J. Am. Chem. Soc. 2005, 127, 16406.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) E. M. Phillips, M. Wadamoto, A. Chan, K. A. Scheidt, Angew. Chem. Int. Ed. 2007, 46, 3107.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) J. J. Song, Z. Tan, J. T. Reeves, D. R. Fandrick, N. K. Yee, C. H. Senanayake, Org. Lett. 2008, 10, 877.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) X.-L. Huang, X.-Y. Chen, S. Ye, J. Org. Chem. 2009, 74, 7585.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) E. M. Phillips, M. Wadamoto, H. S. Roth, K. A. Scheidt, Org. Lett. 2009, 11, 105.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) Y. Kawanaka, E. M. Phillips, K. A. Scheidt, J. Am. Chem. Soc. 2009, 131, 18028.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  (a) J. Castells, H. Llitjos, M. Morenomanas, Tetrahedron Lett. 1977, 18, 205.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) H. Inoue, K. Higashiura, J. Chem. Soc., Chem. Commun. 1980, 12, 549.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) A. Miyashita, Y. Suzuki, I. Nagasaki, C. Ishiguro, K. Iwamoto, T. Higashino, Chem. Pharm. Bull. (Tokyo) 1997, 45, 1254.
      (d) B. E. Maki, A. Chan, E. M. Phillips, K. A. Scheidt, Org. Lett. 2007, 9, 371.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) B. E. Maki, K. A. Scheidt, Org. Lett. 2008, 10, 4331.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) B. E. Maki, A. Chan, E. M. Phillips, K. A. Scheidt, Tetrahedron 2009, 65, 3102.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) S. De Sarkar, S. Grimme, A. Studer, J. Am. Chem. Soc. 2010, 132, 1190.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  (a) K. Morita, Z. Suzuki, H. Hirose, Bull. Chem. Soc. Jpn 1968, 41, 2815.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF1MXlslSkug%3D%3D&md5=a5a46ffb69481fb69eb9b7473871f5aeCAS |
      B. Baylis, M. E. D. Hillman, German Patent 2155113, 1972; Chem. Abstr. 1972, 77, 34174q. For reviews, see:
      (c) S. E. Drewes, G. H. P. Roos, Tetrahedron 1988, 44, 4653.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) D. Basavaiah, P. D. Rao, R. S. Hyma, Tetrahedron 1996, 52, 8001.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) P. Langer, Angew. Chem. Int. Ed. 2000, 39, 3049.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) D. Basavaiah, A. J. Rao, T. Satyanarayana, Chem. Rev. 2003, 103, 811.
         | Crossref | GoogleScholarGoogle Scholar |

[9]  (a) C. Fischer, S. W. Smith, D. A. Powell, G. C. Fu, J. Am. Chem. Soc. 2006, 128, 1472.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XksFSgsQ%3D%3D&md5=882d48962d8c1d91128af5cf212194b3CAS |
      (b) L. He, T.-Y. Jian, S. Ye, J. Org. Chem. 2007, 72, 7466.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  M. M. Rauhut, H. Currier, US Patent 3 074 999, 1963.
      (b) L.-C. Wang, A. L. Luis, K. Agapiou, H.-Y. Jang, M. J. Krische, J. Am. Chem. Soc. 2002, 124, 2402.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) S. A. Frank, D. J. Mergott, W. R. Roush, J. Am. Chem. Soc. 2002, 124, 2404.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) R. K. Thalji, W. R. Roush, J. Am. Chem. Soc. 2005, 127, 16778.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) C. E. Aroyan, S. J. Miller, J. Am. Chem. Soc. 2007, 129, 256.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) F. Seidel, J. A. Gladysz, Synlett 2007, 986.
      (g) T. E. Reynolds, M. S. Binkley, K. A. Scheidt, Org. Lett. 2008, 10, 2449.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) C. E. Aroyan, A. Dermenci, S. J. Miller, Tetrahedron 2009, 65, 4069.
         | Crossref | GoogleScholarGoogle Scholar |

[11]  (a) P. L. Fuchs, T. F. Braish, Chem. Rev. 1986, 86, 903.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL28XlslWnsLg%3D&md5=d262c88ec4f76f4899d561042fc5c78cCAS |
      (b) N. Simpkins, Tetrahedron 1990, 46, 6951.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) K. Grela, M. Bieniek, Tetrahedron Lett. 2001, 42, 6425.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) S. Mossé, A. Alexakis, Org. Lett. 2005, 7, 4361.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) S. Mossé, M. Laars, K. Kriis, T. Kanger, A. Alexakis, Org. Lett. 2006, 8, 2559.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) Q. Zhu, L. Cheng, Y. Lu, Chem. Commun. 2008, 47, 6315.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) Q. Zhu, Y. Lu, Org. Lett. 2008, 10, 4803.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) A. Landa, M. Maestro, C. Masdeu, Á. Puente, S. Vera, M. Oiarbide, C. Palomo, Chemistry 2009, 15, 1562.
         | Crossref | GoogleScholarGoogle Scholar |
      (i) S. Sulzer-Mossé, A. Alexakis, J. Mareda, G. Bollot, G. Bernardinelli, Y. Filinchuk, Chemistry 2009, 15, 3204.
         | Crossref | GoogleScholarGoogle Scholar |
      (j) Q. Zhu, Y. Lu, Org. Lett. 2009, 11, 1721.
         | Crossref | GoogleScholarGoogle Scholar |
      (k) S. A. Moteki, S. Xu, S. Arimitsu, K. Maruoka, J. Am. Chem. Soc. 2010, 132, 17074.
         | Crossref | GoogleScholarGoogle Scholar |
      (l) M. Nielsen, C. B. Jacobsen, N. Holub, M. W. Paixão, K. A. Jørgensen, Angew. Chem. Int. Ed. 2010, 49, 2668.
      (m) A. Quintard, A. Alexakis, C. Mazet, Angew. Chem. Int. Ed. 2011, 50, 1393.
      (n) J. Xiao, Y.-P. Lu, Y.-L. Liu, P.-S. Wong, T.-P. Loh, Org. Lett. 2011, 13, 876.
         | Crossref | GoogleScholarGoogle Scholar |

[12]  R. L. Atienza, H. S. Roth, K. A. Scheidt, Chem. Sci. 2011, 2, 1772.
         | 1:CAS:528:DC%2BC3MXpvFCms78%3D&md5=95a3704962a0be701f6f2c02b99e55a2CAS |

[13]  (a) R. B. Lettan, K. Scheidt, Org. Lett. 2005, 7, 3227.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXlsFKhs7s%3D&md5=1ef5e4d385bb6a60aece24301effb2afCAS |
      (b) A. E. Mattson, A. M. Zuhl, T. E. Reynolds, K. A. Scheidt, J. Am. Chem. Soc. 2006, 128, 4932.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) A. E. Mattson, K. A. Scheidt, J. Am. Chem. Soc. 2007, 129, 4508.
         | Crossref | GoogleScholarGoogle Scholar |

[14]  A. B. Pangborn, M. A. Giardello, R. H. Grubbs, R. K. Rosen, F. J. Timmers, Organometal. 1996, 15, 1518.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XhtVerur0%3D&md5=05809750f95f7ceef0c71d9fa323e35bCAS |

[15]  D. D. Perrin, W. L. Armarego, Purification of Laboratory Chemicals; 3rd Edn, 1988 (Pergamon Press: Oxford).

[16]  H. Stetter, K. Steinbeck, Liebigs Ann. Chem. 1974, 1315.
         | 1:CAS:528:DyaE2cXls12htr8%3D&md5=c10bc2356a7ce8020ec167dcf20e4f17CAS |