Highly stereoselective synthesis of novel α-haloenamides via a mild and efficient hydrohalogenation of ynamides

Organic Letters

Volumn 5, Issue 9, 2003, Pages 1547-1550

  Mulder, Jason A ^a   Kurtz, Kimberly C M ^a   Hsung, Richard P ^a   Coverdale, Heather ^a   Frederick, Michael O ^a   Shen, Lichun ^a   Zificsak, Craig A ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; HALOGEN; MAGNESIUM SALT;

ARTICLE; CHEMICAL REACTION; CHIRALITY; HALOGENATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0141630352     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0300266     Document Type: Article

References (90)

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31. For reviews on ynamines, see: (a) Himbert, G. In Methoden Der Organischen Chemie (Houben-Weyl); Kropf, H., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1993; pp 3267-3443. (b) Collard-Motte, J.; Janousek, Z. Top. Curr. Chem. 1986, 130, 89. (c) Ficini, J. Tetrahedron 1976, 32, 1448.
32. For reviews on ynamines, see: (a) Himbert, G. In Methoden Der Organischen Chemie (Houben-Weyl); Kropf, H., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1993; pp 3267-3443. (b) Collard-Motte, J.; Janousek, Z. Top. Curr. Chem. 1986, 130, 89. (c) Ficini, J. Tetrahedron 1976, 32, 1448.
33. (a) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417.
34. (b) Mulder, J. A.; Hsung, R. P.; Frederick, M. O.; Tracey, M. R.; Zificsak, C. A. Org. Lett. 2002, 4, 1383.
35. (c) Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Douglas, C. J.; Xiong, H. ; Mulder, J. A. Org. Lett. 1999, 1, 1237.
36. Frederick, M. O.; Mulder, J. A., Tracey, M. R.; Hsung, R. P.; Huang, J.; Kurtz, K. C. M.; Shen, L.; Douglas, C. J. Am. Chem. Soc. 2003, 125, 2368.
37. For our original synthesis, see: Wei, L.-L.; Mulder, J. A.; Xiong, H.; Zificsak, C. A.; Douglas, C. J.; Hsung, R. P. Tetrahedron 2001, 57, 459.
38. For a review on synthesis of ynamides, see: Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P. Synlett 2003, in press.
39. For reviews on enamides, see: (a) Rappoport, Z. The chemistry of enamines. In The Chemistry of Functional Groups; John Wiley and Sons: 1994, New York. (b) Whitesell, J. K.; Whitesell, M. A. Synthesis 1983, 517. (c) Hickmott, P. W. Tetrahedron 1982, 38, 1975. (d) Hickmott, P. W. Tetrahedron 1982, 38, 3363. (e) Lenz, G. R. Synthesis 1978, 489.
40. For reviews on enamides, see: (a) Rappoport, Z. The chemistry of enamines. In The Chemistry of Functional Groups; John Wiley and Sons: 1994, New York. (b) Whitesell, J. K.; Whitesell, M. A. Synthesis 1983, 517. (c) Hickmott, P. W. Tetrahedron 1982, 38, 1975. (d) Hickmott, P. W. Tetrahedron 1982, 38, 3363. (e) Lenz, G. R. Synthesis 1978, 489.
41. For reviews on enamides, see: (a) Rappoport, Z. The chemistry of enamines. In The Chemistry of Functional Groups; John Wiley and Sons: 1994, New York. (b) Whitesell, J. K.; Whitesell, M. A. Synthesis 1983, 517. (c) Hickmott, P. W. Tetrahedron 1982, 38, 1975. (d) Hickmott, P. W. Tetrahedron 1982, 38, 3363. (e) Lenz, G. R. Synthesis 1978, 489.
42. For reviews on enamides, see: (a) Rappoport, Z. The chemistry of enamines. In The Chemistry of Functional Groups; John Wiley and Sons: 1994, New York. (b) Whitesell, J. K.; Whitesell, M. A. Synthesis 1983, 517. (c) Hickmott, P. W. Tetrahedron 1982, 38, 1975. (d) Hickmott, P. W. Tetrahedron 1982, 38, 3363. (e) Lenz, G. R. Synthesis 1978, 489.
43. For reviews on enamides, see: (a) Rappoport, Z. The chemistry of enamines. In The Chemistry of Functional Groups; John Wiley and Sons: 1994, New York. (b) Whitesell, J. K.; Whitesell, M. A. Synthesis 1983, 517. (c) Hickmott, P. W. Tetrahedron 1982, 38, 1975. (d) Hickmott, P. W. Tetrahedron 1982, 38, 3363. (e) Lenz, G. R. Synthesis 1978, 489.
44. For recent studies involving enamides, see: a) Fuchs, J. R.; Funk, R. L. Organic Lett. 2001, 3, 3349. (b) Abbiati, G.; Clerici, F.; Gelmi, M. L.; Gambini, A.; Pilati, T. J. Org. Chem. 2001, 66, 6299. (c) Maeng, J.-H.; Funk, R. L. Org. Lett. 2000, 3, 1125. (d) Shen, R.; Porco, Jr., J. A. Org. Lett. 2000, 2, 1333. (e) Bach, T.; Schröder, J.; Brandl, T.; Hecht, J.; Harms, K. Tetrahedron 1998, 54, 4507. (f) Ogawa, T.; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443.
45. For recent studies involving enamides, see: a) Fuchs, J. R.; Funk, R. L. Organic Lett. 2001, 3, 3349. (b) Abbiati, G.; Clerici, F.; Gelmi, M. L.; Gambini, A.; Pilati, T. J. Org. Chem. 2001, 66, 6299. (c) Maeng, J.-H.; Funk, R. L. Org. Lett. 2000, 3, 1125. (d) Shen, R.; Porco, Jr., J. A. Org. Lett. 2000, 2, 1333. (e) Bach, T.; Schröder, J.; Brandl, T.; Hecht, J.; Harms, K. Tetrahedron 1998, 54, 4507. (f) Ogawa, T.; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443.
46. For recent studies involving enamides, see: a) Fuchs, J. R.; Funk, R. L. Organic Lett. 2001, 3, 3349. (b) Abbiati, G.; Clerici, F.; Gelmi, M. L.; Gambini, A.; Pilati, T. J. Org. Chem. 2001, 66, 6299. (c) Maeng, J.-H.; Funk, R. L. Org. Lett. 2000, 3, 1125. (d) Shen, R.; Porco, Jr., J. A. Org. Lett. 2000, 2, 1333. (e) Bach, T.; Schröder, J.; Brandl, T.; Hecht, J.; Harms, K. Tetrahedron 1998, 54, 4507. (f) Ogawa, T.; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443.
47. For recent studies involving enamides, see: a) Fuchs, J. R.; Funk, R. L. Organic Lett. 2001, 3, 3349. (b) Abbiati, G.; Clerici, F.; Gelmi, M. L.; Gambini, A.; Pilati, T. J. Org. Chem. 2001, 66, 6299. (c) Maeng, J.-H.; Funk, R. L. Org. Lett. 2000, 3, 1125. (d) Shen, R.; Porco, Jr., J. A. Org. Lett. 2000, 2, 1333. (e) Bach, T.; Schröder, J.; Brandl, T.; Hecht, J.; Harms, K. Tetrahedron 1998, 54, 4507. (f) Ogawa, T.; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443.
48. For recent studies involving enamides, see: a) Fuchs, J. R.; Funk, R. L. Organic Lett. 2001, 3, 3349. (b) Abbiati, G.; Clerici, F.; Gelmi, M. L.; Gambini, A.; Pilati, T. J. Org. Chem. 2001, 66, 6299. (c) Maeng, J.-H.; Funk, R. L. Org. Lett. 2000, 3, 1125. (d) Shen, R.; Porco, Jr., J. A. Org. Lett. 2000, 2, 1333. (e) Bach, T.; Schröder, J.; Brandl, T.; Hecht, J.; Harms, K. Tetrahedron 1998, 54, 4507. (f) Ogawa, T.; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443.
49. For recent studies involving enamides, see: a) Fuchs, J. R.; Funk, R. L. Organic Lett. 2001, 3, 3349. (b) Abbiati, G.; Clerici, F.; Gelmi, M. L.; Gambini, A.; Pilati, T. J. Org. Chem. 2001, 66, 6299. (c) Maeng, J.-H.; Funk, R. L. Org. Lett. 2000, 3, 1125. (d) Shen, R.; Porco, Jr., J. A. Org. Lett. 2000, 2, 1333. (e) Bach, T.; Schröder, J.; Brandl, T.; Hecht, J.; Harms, K. Tetrahedron 1998, 54, 4507. (f) Ogawa, T.; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443.
50. For recent examples of α-haloenamides (excluding heterocyclic variants), see: (a) Boiko, V. I.; Sinitsa, A. A.; Onys'ko, P. P. Russ. J. Gen. Chem. 1999, 69, 1879. (b) Meier, S.; Werthwein, E. U. Chem. Ber. 1990, 123, 2339. (c) Kondrat'eva, G. Y.; Agafonov, N. E.; Stashina, G. A. Izv. Akad. Nauk, Ser. Khim. 1989, 9, 2038. (d) Ivanov, C.; Dobrev, A.; Nechev, L.; Nikiforov, T. Synth. Commun. 1989, 19, 297. (e) Mironova, D. F.; Loginova, N. A. Ukr. Khim. Zh. 1986, 52, 71. (f) Del'tsova, D. P.; Zeifman, Y. V.; Gambaryan, N. P. Izv. Akad. Nauk, Ser. Khim. 1985, 11, 2533. (g) Bal'on, Y. G.; Moskaleva, R. N. Zh. Org. Khim. 1983, 19, 2456.
51. For recent examples of α-haloenamides (excluding heterocyclic variants), see: (a) Boiko, V. I.; Sinitsa, A. A.; Onys'ko, P. P. Russ. J. Gen. Chem. 1999, 69, 1879. (b) Meier, S.; Werthwein, E. U. Chem. Ber. 1990, 123, 2339. (c) Kondrat'eva, G. Y.; Agafonov, N. E.; Stashina, G. A. Izv. Akad. Nauk, Ser. Khim. 1989, 9, 2038. (d) Ivanov, C.; Dobrev, A.; Nechev, L.; Nikiforov, T. Synth. Commun. 1989, 19, 297. (e) Mironova, D. F.; Loginova, N. A. Ukr. Khim. Zh. 1986, 52, 71. (f) Del'tsova, D. P.; Zeifman, Y. V.; Gambaryan, N. P. Izv. Akad. Nauk, Ser. Khim. 1985, 11, 2533. (g) Bal'on, Y. G.; Moskaleva, R. N. Zh. Org. Khim. 1983, 19, 2456.
52. For recent examples of α-haloenamides (excluding heterocyclic variants), see: (a) Boiko, V. I.; Sinitsa, A. A.; Onys'ko, P. P. Russ. J. Gen. Chem. 1999, 69, 1879. (b) Meier, S.; Werthwein, E. U. Chem. Ber. 1990, 123, 2339. (c) Kondrat'eva, G. Y.; Agafonov, N. E.; Stashina, G. A. Izv. Akad. Nauk, Ser. Khim. 1989, 9, 2038. (d) Ivanov, C.; Dobrev, A.; Nechev, L.; Nikiforov, T. Synth. Commun. 1989, 19, 297. (e) Mironova, D. F.; Loginova, N. A. Ukr. Khim. Zh. 1986, 52, 71. (f) Del'tsova, D. P.; Zeifman, Y. V.; Gambaryan, N. P. Izv. Akad. Nauk, Ser. Khim. 1985, 11, 2533. (g) Bal'on, Y. G.; Moskaleva, R. N. Zh. Org. Khim. 1983, 19, 2456.
53. For recent examples of α-haloenamides (excluding heterocyclic variants), see: (a) Boiko, V. I.; Sinitsa, A. A.; Onys'ko, P. P. Russ. J. Gen. Chem. 1999, 69, 1879. (b) Meier, S.; Werthwein, E. U. Chem. Ber. 1990, 123, 2339. (c) Kondrat'eva, G. Y.; Agafonov, N. E.; Stashina, G. A. Izv. Akad. Nauk, Ser. Khim. 1989, 9, 2038. (d) Ivanov, C.; Dobrev, A.; Nechev, L.; Nikiforov, T. Synth. Commun. 1989, 19, 297. (e) Mironova, D. F.; Loginova, N. A. Ukr. Khim. Zh. 1986, 52, 71. (f) Del'tsova, D. P.; Zeifman, Y. V.; Gambaryan, N. P. Izv. Akad. Nauk, Ser. Khim. 1985, 11, 2533. (g) Bal'on, Y. G.; Moskaleva, R. N. Zh. Org. Khim. 1983, 19, 2456.
54. For recent examples of α-haloenamides (excluding heterocyclic variants), see: (a) Boiko, V. I.; Sinitsa, A. A.; Onys'ko, P. P. Russ. J. Gen. Chem. 1999, 69, 1879. (b) Meier, S.; Werthwein, E. U. Chem. Ber. 1990, 123, 2339. (c) Kondrat'eva, G. Y.; Agafonov, N. E.; Stashina, G. A. Izv. Akad. Nauk, Ser. Khim. 1989, 9, 2038. (d) Ivanov, C.; Dobrev, A.; Nechev, L.; Nikiforov, T. Synth. Commun. 1989, 19, 297. (e) Mironova, D. F.; Loginova, N. A. Ukr. Khim. Zh. 1986, 52, 71. (f) Del'tsova, D. P.; Zeifman, Y. V.; Gambaryan, N. P. Izv. Akad. Nauk, Ser. Khim. 1985, 11, 2533. (g) Bal'on, Y. G.; Moskaleva, R. N. Zh. Org. Khim. 1983, 19, 2456.
55. For recent examples of α-haloenamides (excluding heterocyclic variants), see: (a) Boiko, V. I.; Sinitsa, A. A.; Onys'ko, P. P. Russ. J. Gen. Chem. 1999, 69, 1879. (b) Meier, S.; Werthwein, E. U. Chem. Ber. 1990, 123, 2339. (c) Kondrat'eva, G. Y.; Agafonov, N. E.; Stashina, G. A. Izv. Akad. Nauk, Ser. Khim. 1989, 9, 2038. (d) Ivanov, C.; Dobrev, A.; Nechev, L.; Nikiforov, T. Synth. Commun. 1989, 19, 297. (e) Mironova, D. F.; Loginova, N. A. Ukr. Khim. Zh. 1986, 52, 71. (f) Del'tsova, D. P.; Zeifman, Y. V.; Gambaryan, N. P. Izv. Akad. Nauk, Ser. Khim. 1985, 11, 2533. (g) Bal'on, Y. G.; Moskaleva, R. N. Zh. Org. Khim. 1983, 19, 2456.
56. For recent examples of α-haloenamides (excluding heterocyclic variants), see: (a) Boiko, V. I.; Sinitsa, A. A.; Onys'ko, P. P. Russ. J. Gen. Chem. 1999, 69, 1879. (b) Meier, S.; Werthwein, E. U. Chem. Ber. 1990, 123, 2339. (c) Kondrat'eva, G. Y.; Agafonov, N. E.; Stashina, G. A. Izv. Akad. Nauk, Ser. Khim. 1989, 9, 2038. (d) Ivanov, C.; Dobrev, A.; Nechev, L.; Nikiforov, T. Synth. Commun. 1989, 19, 297. (e) Mironova, D. F.; Loginova, N. A. Ukr. Khim. Zh. 1986, 52, 71. (f) Del'tsova, D. P.; Zeifman, Y. V.; Gambaryan, N. P. Izv. Akad. Nauk, Ser. Khim. 1985, 11, 2533. (g) Bal'on, Y. G.; Moskaleva, R. N. Zh. Org. Khim. 1983, 19, 2456.
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60. Chiral and achiral α-halo vinyl ethers: (a) Yu, W.; Jin, Z. J. Am. Chem. Soc. 2000, 122, 9840. Applications in synthesis: (b) Yu, Z.; Jin, Z. J. Am. Chem. Soc. 2001, 123, 3369. (c) Yu, Z.; Jin, Z. J. Am. Chem. Soc. 2002, 124, 6576. (d) Su, M.; Kang, Y.; Yu, W.; Hua, Z.; Jin, Z. Org. Lett. 2002, 4, 691. α-Halo vinyl sulfides: Su, M.; Yu, W.; Jin, Z. Tetrahedron Lett. 2001, 42, 3771.
61. Chiral and achiral α-halo vinyl ethers: (a) Yu, W.; Jin, Z. J. Am. Chem. Soc. 2000, 122, 9840. Applications in synthesis: (b) Yu, Z.; Jin, Z. J. Am. Chem. Soc. 2001, 123, 3369. (c) Yu, Z.; Jin, Z. J. Am. Chem. Soc. 2002, 124, 6576. (d) Su, M.; Kang, Y.; Yu, W.; Hua, Z.; Jin, Z. Org. Lett. 2002, 4, 691. α-Halo vinyl sulfides: Su, M.; Yu, W.; Jin, Z. Tetrahedron Lett. 2001, 42, 3771.
62. Chiral and achiral α-halo vinyl ethers: (a) Yu, W.; Jin, Z. J. Am. Chem. Soc. 2000, 122, 9840. Applications in synthesis: (b) Yu, Z.; Jin, Z. J. Am. Chem. Soc. 2001, 123, 3369. (c) Yu, Z.; Jin, Z. J. Am. Chem. Soc. 2002, 124, 6576. (d) Su, M.; Kang, Y.; Yu, W.; Hua, Z.; Jin, Z. Org. Lett. 2002, 4, 691. α-Halo vinyl sulfides: Su, M.; Yu, W.; Jin, Z. Tetrahedron Lett. 2001, 42, 3771.
63. Chiral and achiral α-halo vinyl ethers: (a) Yu, W.; Jin, Z. J. Am. Chem. Soc. 2000, 122, 9840. Applications in synthesis: (b) Yu, Z.; Jin, Z. J. Am. Chem. Soc. 2001, 123, 3369. (c) Yu, Z.; Jin, Z. J. Am. Chem. Soc. 2002, 124, 6576. (d) Su, M.; Kang, Y.; Yu, W.; Hua, Z.; Jin, Z. Org. Lett. 2002, 4, 691. α-Halo vinyl sulfides: Su, M.; Yu, W.; Jin, Z. Tetrahedron Lett. 2001, 42, 3771.
64. Chiral and achiral α-halo vinyl ethers: (a) Yu, W.; Jin, Z. J. Am. Chem. Soc. 2000, 122, 9840. Applications in synthesis: (b) Yu, Z.; Jin, Z. J. Am. Chem. Soc. 2001, 123, 3369. (c) Yu, Z.; Jin, Z. J. Am. Chem. Soc. 2002, 124, 6576. (d) Su, M.; Kang, Y.; Yu, W.; Hua, Z.; Jin, Z. Org. Lett. 2002, 4, 691. α-Halo vinyl sulfides: Su, M.; Yu, W.; Jin, Z. Tetrahedron Lett. 2001, 42, 3771.
65. Other recent examples for α-halo vinyl ethers: (a) Bacilieri, C.; Reic, S.; Neuenschwander, M. Helv. Chim. Acta 2000, 83, 1182. (b) Glazunova, E. Y.; Lutsenko, S. V.; Efimova, I. V.; Trostyanskaya, I. G.; Kazankova, M. A.; Beletskaya, I. P. Russ. J. Org. Chem. 1969, 34, 1104. α-Halo vinyl sulfides: (c) Duncan, D.; Livinghouse, T. J. Org. Chem. 2001, 66, 5237. (d) Stefani, H. A.; Comasseto, J. V.; Petragnani, N. Braga, A. L.; Menezes, P. H. Gusevskaya, E. V. Phosporus, Sulfur Silicon Relat. Elem. 1997, 126, 211. α-Halo vinyl sulfates: (e) Paley, R. S.; Dios, A. de; Estroff, L. A.; Lafontine, J. A.; Montero, C. et al. J. Org. Chem. 1997, 62, 6326. (f) Zhong, P.; Huang, X.; Ping-Guo, M. Tetrahedron 2000, 56, 8921. α-Halo vinyl phosphonates: (g) Kobayashi, Y.; William, A. D. Org. Lett. 2002, 4, 4241. (h) Zhang, X.; Burton, D. J. J. Fluorine Chem. 2001, 112, 47.
66. Other recent examples for α-halo vinyl ethers: (a) Bacilieri, C.; Reic, S.; Neuenschwander, M. Helv. Chim. Acta 2000, 83, 1182. (b) Glazunova, E. Y.; Lutsenko, S. V.; Efimova, I. V.; Trostyanskaya, I. G.; Kazankova, M. A.; Beletskaya, I. P. Russ. J. Org. Chem. 1969, 34, 1104. α-Halo vinyl sulfides: (c) Duncan, D.; Livinghouse, T. J. Org. Chem. 2001, 66, 5237. (d) Stefani, H. A.; Comasseto, J. V.; Petragnani, N. Braga, A. L.; Menezes, P. H. Gusevskaya, E. V. Phosporus, Sulfur Silicon Relat. Elem. 1997, 126, 211. α-Halo vinyl sulfates: (e) Paley, R. S.; Dios, A. de; Estroff, L. A.; Lafontine, J. A.; Montero, C. et al. J. Org. Chem. 1997, 62, 6326. (f) Zhong, P.; Huang, X.; Ping-Guo, M. Tetrahedron 2000, 56, 8921. α-Halo vinyl phosphonates: (g) Kobayashi, Y.; William, A. D. Org. Lett. 2002, 4, 4241. (h) Zhang, X.; Burton, D. J. J. Fluorine Chem. 2001, 112, 47.
67. Other recent examples for α-halo vinyl ethers: (a) Bacilieri, C.; Reic, S.; Neuenschwander, M. Helv. Chim. Acta 2000, 83, 1182. (b) Glazunova, E. Y.; Lutsenko, S. V.; Efimova, I. V.; Trostyanskaya, I. G.; Kazankova, M. A.; Beletskaya, I. P. Russ. J. Org. Chem. 1969, 34, 1104. α-Halo vinyl sulfides: (c) Duncan, D.; Livinghouse, T. J. Org. Chem. 2001, 66, 5237. (d) Stefani, H. A.; Comasseto, J. V.; Petragnani, N. Braga, A. L.; Menezes, P. H. Gusevskaya, E. V. Phosporus, Sulfur Silicon Relat. Elem. 1997, 126, 211. α-Halo vinyl sulfates: (e) Paley, R. S.; Dios, A. de; Estroff, L. A.; Lafontine, J. A.; Montero, C. et al. J. Org. Chem. 1997, 62, 6326. (f) Zhong, P.; Huang, X.; Ping-Guo, M. Tetrahedron 2000, 56, 8921. α-Halo vinyl phosphonates: (g) Kobayashi, Y.; William, A. D. Org. Lett. 2002, 4, 4241. (h) Zhang, X.; Burton, D. J. J. Fluorine Chem. 2001, 112, 47.
68. Other recent examples for α-halo vinyl ethers: (a) Bacilieri, C.; Reic, S.; Neuenschwander, M. Helv. Chim. Acta 2000, 83, 1182. (b) Glazunova, E. Y.; Lutsenko, S. V.; Efimova, I. V.; Trostyanskaya, I. G.; Kazankova, M. A.; Beletskaya, I. P. Russ. J. Org. Chem. 1969, 34, 1104. α-Halo vinyl sulfides: (c) Duncan, D.; Livinghouse, T. J. Org. Chem. 2001, 66, 5237. (d) Stefani, H. A.; Comasseto, J. V.; Petragnani, N. Braga, A. L.; Menezes, P. H. Gusevskaya, E. V. Phosporus, Sulfur Silicon Relat. Elem. 1997, 126, 211. α-Halo vinyl sulfates: (e) Paley, R. S.; Dios, A. de; Estroff, L. A.; Lafontine, J. A.; Montero, C. et al. J. Org. Chem. 1997, 62, 6326. (f) Zhong, P.; Huang, X.; Ping-Guo, M. Tetrahedron 2000, 56, 8921. α-Halo vinyl phosphonates: (g) Kobayashi, Y.; William, A. D. Org. Lett. 2002, 4, 4241. (h) Zhang, X.; Burton, D. J. J. Fluorine Chem. 2001, 112, 47.
69. Other recent examples for α-halo vinyl ethers: (a) Bacilieri, C.; Reic, S.; Neuenschwander, M. Helv. Chim. Acta 2000, 83, 1182. (b) Glazunova, E. Y.; Lutsenko, S. V.; Efimova, I. V.; Trostyanskaya, I. G.; Kazankova, M. A.; Beletskaya, I. P. Russ. J. Org. Chem. 1969, 34, 1104. α-Halo vinyl sulfides: (c) Duncan, D.; Livinghouse, T. J. Org. Chem. 2001, 66, 5237. (d) Stefani, H. A.; Comasseto, J. V.; Petragnani, N. Braga, A. L.; Menezes, P. H. Gusevskaya, E. V. Phosporus, Sulfur Silicon Relat. Elem. 1997, 126, 211. α-Halo vinyl sulfates: (e) Paley, R. S.; Dios, A. de; Estroff, L. A.; Lafontine, J. A.; Montero, C. et al. J. Org. Chem. 1997, 62, 6326. (f) Zhong, P.; Huang, X.; Ping-Guo, M. Tetrahedron 2000, 56, 8921. α-Halo vinyl phosphonates: (g) Kobayashi, Y.; William, A. D. Org. Lett. 2002, 4, 4241. (h) Zhang, X.; Burton, D. J. J. Fluorine Chem. 2001, 112, 47.
70. Other recent examples for α-halo vinyl ethers: (a) Bacilieri, C.; Reic, S.; Neuenschwander, M. Helv. Chim. Acta 2000, 83, 1182. (b) Glazunova, E. Y.; Lutsenko, S. V.; Efimova, I. V.; Trostyanskaya, I. G.; Kazankova, M. A.; Beletskaya, I. P. Russ. J. Org. Chem. 1969, 34, 1104. α-Halo vinyl sulfides: (c) Duncan, D.; Livinghouse, T. J. Org. Chem. 2001, 66, 5237. (d) Stefani, H. A.; Comasseto, J. V.; Petragnani, N. Braga, A. L.; Menezes, P. H. Gusevskaya, E. V. Phosporus, Sulfur Silicon Relat. Elem. 1997, 126, 211. α-Halo vinyl sulfates: (e) Paley, R. S.; Dios, A. de; Estroff, L. A.; Lafontine, J. A.; Montero, C. et al. J. Org. Chem. 1997, 62, 6326. (f) Zhong, P.; Huang, X.; Ping-Guo, M. Tetrahedron 2000, 56, 8921. α-Halo vinyl phosphonates: (g) Kobayashi, Y.; William, A. D. Org. Lett. 2002, 4, 4241. (h) Zhang, X.; Burton, D. J. J. Fluorine Chem. 2001, 112, 47.
71. Other recent examples for α-halo vinyl ethers: (a) Bacilieri, C.; Reic, S.; Neuenschwander, M. Helv. Chim. Acta 2000, 83, 1182. (b) Glazunova, E. Y.; Lutsenko, S. V.; Efimova, I. V.; Trostyanskaya, I. G.; Kazankova, M. A.; Beletskaya, I. P. Russ. J. Org. Chem. 1969, 34, 1104. α-Halo vinyl sulfides: (c) Duncan, D.; Livinghouse, T. J. Org. Chem. 2001, 66, 5237. (d) Stefani, H. A.; Comasseto, J. V.; Petragnani, N. Braga, A. L.; Menezes, P. H. Gusevskaya, E. V. Phosporus, Sulfur Silicon Relat. Elem. 1997, 126, 211. α-Halo vinyl sulfates: (e) Paley, R. S.; Dios, A. de; Estroff, L. A.; Lafontine, J. A.; Montero, C. et al. J. Org. Chem. 1997, 62, 6326. (f) Zhong, P.; Huang, X.; Ping-Guo, M. Tetrahedron 2000, 56, 8921. α-Halo vinyl phosphonates: (g) Kobayashi, Y.; William, A. D. Org. Lett. 2002, 4, 4241. (h) Zhang, X.; Burton, D. J. J. Fluorine Chem. 2001, 112, 47.
72. Other recent examples for α-halo vinyl ethers: (a) Bacilieri, C.; Reic, S.; Neuenschwander, M. Helv. Chim. Acta 2000, 83, 1182. (b) Glazunova, E. Y.; Lutsenko, S. V.; Efimova, I. V.; Trostyanskaya, I. G.; Kazankova, M. A.; Beletskaya, I. P. Russ. J. Org. Chem. 1969, 34, 1104. α-Halo vinyl sulfides: (c) Duncan, D.; Livinghouse, T. J. Org. Chem. 2001, 66, 5237. (d) Stefani, H. A.; Comasseto, J. V.; Petragnani, N. Braga, A. L.; Menezes, P. H. Gusevskaya, E. V. Phosporus, Sulfur Silicon Relat. Elem. 1997, 126, 211. α-Halo vinyl sulfates: (e) Paley, R. S.; Dios, A. de; Estroff, L. A.; Lafontine, J. A.; Montero, C. et al. J. Org. Chem. 1997, 62, 6326. (f) Zhong, P.; Huang, X.; Ping-Guo, M. Tetrahedron 2000, 56, 8921. α-Halo vinyl phosphonates: (g) Kobayashi, Y.; William, A. D. Org. Lett. 2002, 4, 4241. (h) Zhang, X.; Burton, D. J. J. Fluorine Chem. 2001, 112, 47.
73. For a review on thermal [2 + 2] cycloaddition reactions, see: Baldwin, J. E. Comprehensive Organic Synthesis; Trost, B. M. Fleming, I.; Pattenden, G., Eds.; Pergamon Press: New York, 1991, Vol. 5, p 63.
74. For examples of [2 + 2] cycloaddition reaction of ynamines with enones see: (a) Ficini, J.; Krief, A.; Guingant, A.; Desmaele, D. Tetrahedron Lett. 1981, 725. (b) Ficini, J.; Guingant, A.; d'Angelo, J.; Stork, G. Tetrahedron Lett. 1983, 907.
75. For examples of [2 + 2] cycloaddition reaction of ynamines with enones see: (a) Ficini, J.; Krief, A.; Guingant, A.; Desmaele, D. Tetrahedron Lett. 1981, 725. (b) Ficini, J.; Guingant, A.; d'Angelo, J.; Stork, G. Tetrahedron Lett. 1983, 907.
76. D.
77. Assigned later by correlating with X-ray structure of α-haloenamide 26.
78. (a) Evans, D. A. Aldrichimica Acta 1982, 15, 23.
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87. Examples of enynes in Diels Alder reactions: (a) Hoffmann, H. M. R.; Mucha, B.; Oehlerking, H. H.; Prahst, G. W. Tetrahedron 1993, 49, 8999. (b) Spino, C.; Crawford, J. Tetrahedron Lett. 1994, 35, 5559. (c) Burrell, R. C.; Daoust, K. J.; Bradley, A. Z.; DiRico, K. J.; Johnson, R. P. J. Am. Chem. Soc. 1996, 118, 4218.
88. Examples of enynes in Diels Alder reactions: (a) Hoffmann, H. M. R.; Mucha, B.; Oehlerking, H. H.; Prahst, G. W. Tetrahedron 1993, 49, 8999. (b) Spino, C.; Crawford, J. Tetrahedron Lett. 1994, 35, 5559. (c) Burrell, R. C.; Daoust, K. J.; Bradley, A. Z.; DiRico, K. J.; Johnson, R. P. J. Am. Chem. Soc. 1996, 118, 4218.
89. Examples of enynes in Diels Alder reactions: (a) Hoffmann, H. M. R.; Mucha, B.; Oehlerking, H. H.; Prahst, G. W. Tetrahedron 1993, 49, 8999. (b) Spino, C.; Crawford, J. Tetrahedron Lett. 1994, 35, 5559. (c) Burrell, R. C.; Daoust, K. J.; Bradley, A. Z.; DiRico, K. J.; Johnson, R. P. J. Am. Chem. Soc. 1996, 118, 4218.
90. Xiong, H.; Hsung, R. P.; Shen, L.; Hahn, J. M. Tetrahedron Lett. 2002, 43, 4449.