Aza-Baylis-Hillman reactions of N-(arylmethylene) diphenylphosphinamides with activated olefins in the presence of various Lewis bases

Advanced Synthesis and Catalysis

Volumn 346, Issue 9-10, 2004, Pages 1205-1219

  Shi, Min ^a   Zhao, Gui Ling ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Aza Baylis Hillman reactions; DABCO, Lewis bases; N (arylmethylene)diphenylphosphinamide; Organic catalysis; Phosphanes

Indexed keywords

2 CYCLOHEXENONE; 2 CYCLOPENTEN 1 ONE; ACRYLIC ACID DERIVATIVE; ACRYLIC ACID METHYL ESTER; ACRYLONITRILE; AMIDE; KETONE DERIVATIVE; NITROGEN; PHOSPHINE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; BAYLIS HILLMAN REACTION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 5144223758     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404081     Document Type: Article

References (61)

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28. Baylis-Hillman reactions using sulfonated imines or phosphorylated imines as the substrate can be named as aza-Baylis-Hillman reactions. For previous reports related with the Baylis-Hillman reactions of methyl acrylate with imines, please see: a) P. Perlmutter, C. C. Teo, Tetrahedron Lett. 1984, 25, 5951-5952; b) M. Takagi, K. Yamamoto, Tetrahedron 1991, 47, 8869-8882;
29. Baylis-Hillman reactions using sulfonated imines or phosphorylated imines as the substrate can be named as aza-Baylis-Hillman reactions. For previous reports related with the Baylis-Hillman reactions of methyl acrylate with imines, please see: a) P. Perlmutter, C. C. Teo, Tetrahedron Lett. 1984, 25, 5951-5952; b) M. Takagi, K. Yamamoto, Tetrahedron 1991, 47, 8869-8882;
30. For previous reports related with the Baylis-Hillman reactions of MVK with imines generated in situ, please see: c) S. Bertenshow, M. Kahn, Tetrahedron Lett. 1989, 30, 2731-2732; d) D. Balan, H. Adolfsson, J. Org. Chem. 2002, 67, 2329-2334 and references cited therein.
31. For previous reports related with the Baylis-Hillman reactions of MVK with imines generated in situ, please see: c) S. Bertenshow, M. Kahn, Tetrahedron Lett. 1989, 30, 2731-2732; d) D. Balan, H. Adolfsson, J. Org. Chem. 2002, 67, 2329-2334 and references cited therein.
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39. N-(Arylmethylene)diphenylphosphinamides 1 were prepared according to the literature: a) W. B. Jennings, C. J. Lovely, Tetrahedron 1991, 47, 5561-5568; b) K. Yamada, S. J. Harwood, H. Groger, M. Shibasaki, Angew. Chem. Int. Ed. 1999, 38, 3504-3506.
40. N-(Arylmethylene)diphenylphosphinamides 1 were prepared according to the literature: a) W. B. Jennings, C. J. Lovely, Tetrahedron 1991, 47, 5561-5568; b) K. Yamada, S. J. Harwood, H. Groger, M. Shibasaki, Angew. Chem. Int. Ed. 1999, 38, 3504-3506.
41. 3 N has been disclosed: M. Shi, G.-L. Zhao, Tetrahedron Lett. 2002, 43, 9171-9174.
42. For the double Baylis-Hillman reactions, please see: a) M. Shi, C.-Q. Li, J.-K. Jiang, Chem. Commun. 2001, 833-834 (double Baylis-Hillman adduct in the reaction of aryl aldehyde with excess of MVK in the presence of the nitrogen Lewis base DABCO); b) M. Shi, C.-Q. Li, J.-K. Jiang, Helve. Chem. Acta 2002, 85, 1051-1057 (double Baylis-Hillman adduct in the reaction of aryl aldehyde with excess of PVK in the presence of the nitrogen Lewis base DABCO); c) M. Shi, Y.-M. Xu, J. Org. Chem. 2003, 68, 4784-4790 (double aza-Baylis-Hillman adduct in the reaction of N-tosyl imine with excess of phenyl vinyl ketone (PVK) in the presence of the nitrogen Lewis base DABCO).
43. For the double Baylis-Hillman reactions, please see: a) M. Shi, C.-Q. Li, J.-K. Jiang, Chem. Commun. 2001, 833-834 (double Baylis-Hillman adduct in the reaction of aryl aldehyde with excess of MVK in the presence of the nitrogen Lewis base DABCO); b) M. Shi, C.-Q. Li, J.-K. Jiang, Helve. Chem. Acta 2002, 85, 1051-1057 (double Baylis-Hillman adduct in the reaction of aryl aldehyde with excess of PVK in the presence of the nitrogen Lewis base DABCO); c) M. Shi, Y.-M. Xu, J. Org. Chem. 2003, 68, 4784-4790 (double aza-Baylis-Hillman adduct in the reaction of N-tosyl imine with excess of phenyl vinyl ketone (PVK) in the presence of the nitrogen Lewis base DABCO).
44. For the double Baylis-Hillman reactions, please see: a) M. Shi, C.-Q. Li, J.-K. Jiang, Chem. Commun. 2001, 833-834 (double Baylis-Hillman adduct in the reaction of aryl aldehyde with excess of MVK in the presence of the nitrogen Lewis base DABCO); b) M. Shi, C.-Q. Li, J.-K. Jiang, Helve. Chem. Acta 2002, 85, 1051-1057 (double Baylis-Hillman adduct in the reaction of aryl aldehyde with excess of PVK in the presence of the nitrogen Lewis base DABCO); c) M. Shi, Y.-M. Xu, J. Org. Chem. 2003, 68, 4784-4790 (double aza-Baylis-Hillman adduct in the reaction of N-tosyl imine with excess of phenyl vinyl ketone (PVK) in the presence of the nitrogen Lewis base DABCO).
45. 000 = 1144; diffractometer: Rigaku AFC7R, residuals: R, Rw: 0.0596, 0.1531.
46. 000 = 1064, diffractometer: Rigaku AFC7R, residuals: R, Rw: 0.0552, 0.1087.
47. For the reactions employing an enolate as a general base, please see: a) D. A. White, M. M. Baizer, Tetrahedron Lett. 1973, 3597; b) I. C. Stewart, R. G. Bergman, F. D. Toste, J. Am. Chem. Soc. 2003, 125, 8696; c) J. Inanaga, Y. Baba, T. Hanamoto, Chemistry Lett. 1993, 241; d) I. Yavari, R. Hekmat-Shoar, A. Zonouzi, Tetrahedron Lett. 1998, 39, 2391; e) R. B. Grossman, D. S. Pendharkar, B. O. Patrick, J. Org. Chem. 1999, 64, 7178; f) R. B. Grossman, S. Comesse, R. M. Rasne, K. Hattori, M. N. Delong, J. Org. Chem. 2003, 68, 871.
48. For the reactions employing an enolate as a general base, please see: a) D. A. White, M. M. Baizer, Tetrahedron Lett. 1973, 3597; b) I. C. Stewart, R. G. Bergman, F. D. Toste, J. Am. Chem. Soc. 2003, 125, 8696; c) J. Inanaga, Y. Baba, T. Hanamoto, Chemistry Lett. 1993, 241; d) I. Yavari, R. Hekmat-Shoar, A. Zonouzi, Tetrahedron Lett. 1998, 39, 2391; e) R. B. Grossman, D. S. Pendharkar, B. O. Patrick, J. Org. Chem. 1999, 64, 7178; f) R. B. Grossman, S. Comesse, R. M. Rasne, K. Hattori, M. N. Delong, J. Org. Chem. 2003, 68, 871.
49. For the reactions employing an enolate as a general base, please see: a) D. A. White, M. M. Baizer, Tetrahedron Lett. 1973, 3597; b) I. C. Stewart, R. G. Bergman, F. D. Toste, J. Am. Chem. Soc. 2003, 125, 8696; c) J. Inanaga, Y. Baba, T. Hanamoto, Chemistry Lett. 1993, 241; d) I. Yavari, R. Hekmat-Shoar, A. Zonouzi, Tetrahedron Lett. 1998, 39, 2391; e) R. B. Grossman, D. S. Pendharkar, B. O. Patrick, J. Org. Chem. 1999, 64, 7178; f) R. B. Grossman, S. Comesse, R. M. Rasne, K. Hattori, M. N. Delong, J. Org. Chem. 2003, 68, 871.
50. For the reactions employing an enolate as a general base, please see: a) D. A. White, M. M. Baizer, Tetrahedron Lett. 1973, 3597; b) I. C. Stewart, R. G. Bergman, F. D. Toste, J. Am. Chem. Soc. 2003, 125, 8696; c) J. Inanaga, Y. Baba, T. Hanamoto, Chemistry Lett. 1993, 241; d) I. Yavari, R. Hekmat-Shoar, A. Zonouzi, Tetrahedron Lett. 1998, 39, 2391; e) R. B. Grossman, D. S. Pendharkar, B. O. Patrick, J. Org. Chem. 1999, 64, 7178; f) R. B. Grossman, S. Comesse, R. M. Rasne, K. Hattori, M. N. Delong, J. Org. Chem. 2003, 68, 871.
51. For the reactions employing an enolate as a general base, please see: a) D. A. White, M. M. Baizer, Tetrahedron Lett. 1973, 3597; b) I. C. Stewart, R. G. Bergman, F. D. Toste, J. Am. Chem. Soc. 2003, 125, 8696; c) J. Inanaga, Y. Baba, T. Hanamoto, Chemistry Lett. 1993, 241; d) I. Yavari, R. Hekmat-Shoar, A. Zonouzi, Tetrahedron Lett. 1998, 39, 2391; e) R. B. Grossman, D. S. Pendharkar, B. O. Patrick, J. Org. Chem. 1999, 64, 7178; f) R. B. Grossman, S. Comesse, R. M. Rasne, K. Hattori, M. N. Delong, J. Org. Chem. 2003, 68, 871.
52. For the reactions employing an enolate as a general base, please see: a) D. A. White, M. M. Baizer, Tetrahedron Lett. 1973, 3597; b) I. C. Stewart, R. G. Bergman, F. D. Toste, J. Am. Chem. Soc. 2003, 125, 8696; c) J. Inanaga, Y. Baba, T. Hanamoto, Chemistry Lett. 1993, 241; d) I. Yavari, R. Hekmat-Shoar, A. Zonouzi, Tetrahedron Lett. 1998, 39, 2391; e) R. B. Grossman, D. S. Pendharkar, B. O. Patrick, J. Org. Chem. 1999, 64, 7178; f) R. B. Grossman, S. Comesse, R. M. Rasne, K. Hattori, M. N. Delong, J. Org. Chem. 2003, 68, 871.
53. [9c]
54. 000 = 620; diffractometer: Rigaku AFC7R, residuals: R, Rw: 0.0695, 0.1730.
55. For references related to the proposed mechanism for the formation of 12, invoking a 1,2-prototropic shift, please see a) B. M. Trost, U. Kazmaier, J. Am. Chem. Soc. 1992, 114, 7933; b) X. Lu, C. Zhang, Z. Xu, Acc. Chem. Res. 2001, 34, 535; c) B. M. Trost, C.-J. Li, J. Am. Chem. Soc. 1994, 116, 3167; d) B. M. Trost, G. R. Dake, J. Am. Chem. Soc. 1997, 119, 7595; e) C. Zhang, X. Lu, J. Org. Chem. 1995, 60, 2906.
56. For references related to the proposed mechanism for the formation of 12, invoking a 1,2-prototropic shift, please see a) B. M. Trost, U. Kazmaier, J. Am. Chem. Soc. 1992, 114, 7933; b) X. Lu, C. Zhang, Z. Xu, Acc. Chem. Res. 2001, 34, 535; c) B. M. Trost, C.-J. Li, J. Am. Chem. Soc. 1994, 116, 3167; d) B. M. Trost, G. R. Dake, J. Am. Chem. Soc. 1997, 119, 7595; e) C. Zhang, X. Lu, J. Org. Chem. 1995, 60, 2906.
57. For references related to the proposed mechanism for the formation of 12, invoking a 1,2-prototropic shift, please see a) B. M. Trost, U. Kazmaier, J. Am. Chem. Soc. 1992, 114, 7933; b) X. Lu, C. Zhang, Z. Xu, Acc. Chem. Res. 2001, 34, 535; c) B. M. Trost, C.-J. Li, J. Am. Chem. Soc. 1994, 116, 3167; d) B. M. Trost, G. R. Dake, J. Am. Chem. Soc. 1997, 119, 7595; e) C. Zhang, X. Lu, J. Org. Chem. 1995, 60, 2906.
58. For references related to the proposed mechanism for the formation of 12, invoking a 1,2-prototropic shift, please see a) B. M. Trost, U. Kazmaier, J. Am. Chem. Soc. 1992, 114, 7933; b) X. Lu, C. Zhang, Z. Xu, Acc. Chem. Res. 2001, 34, 535; c) B. M. Trost, C.-J. Li, J. Am. Chem. Soc. 1994, 116, 3167; d) B. M. Trost, G. R. Dake, J. Am. Chem. Soc. 1997, 119, 7595; e) C. Zhang, X. Lu, J. Org. Chem. 1995, 60, 2906.
59. For references related to the proposed mechanism for the formation of 12, invoking a 1,2-prototropic shift, please see a) B. M. Trost, U. Kazmaier, J. Am. Chem. Soc. 1992, 114, 7933; b) X. Lu, C. Zhang, Z. Xu, Acc. Chem. Res. 2001, 34, 535; c) B. M. Trost, C.-J. Li, J. Am. Chem. Soc. 1994, 116, 3167; d) B. M. Trost, G. R. Dake, J. Am. Chem. Soc. 1997, 119, 7595; e) C. Zhang, X. Lu, J. Org. Chem. 1995, 60, 2906.
60. The catalyst TQO was first prepared by Prof. Hoffman: C. von Riesen, H. M. R. Hoffmann, Chem. Eur. J. 1996, 2, 680-684.
61. Hatakayama has reported the catalytic, asymmetric Baylis-Hillman reactions of aromatic imines with 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) in the presence of β-isocupreidine (β-ICD) (TQO): S. Kawahara, A. Nakano, T. Esumi, Y. Iwabuchi, S. Hatakayama, Org. Lett. 2003, 5, 3103-3105.