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Organic Letters

Volumn 6, Issue 5, 2004, Pages 699-702

Hetero Diels-Alder reactions of nitrosoamidines: An efficient method for the synthesis of functionalized guanidines

(2) Miller, Craig A a Batey, Robert A a

a UNIVERSITY OF TORONTO (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDINE; GUANIDINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; DIELS ALDER REACTION; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

AMIDINES; CYCLIZATION; GUANIDINES; MOLECULAR STRUCTURE; NITROSO COMPOUNDS;

EID: 1642365600 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol0363117 Document Type: Article

Times cited : (39)

References (40)

1
- 0000104010
- Wichterle, O. Collect. Czech. Chem. Commun. 1947, 12, 292-299.
- (1947) Collect. Czech. Chem. Commun. , vol.12 , pp. 292-299
- Wichterle, O.¹

2
- 0010745317
- Kirby, G. W. Chem. Soc. Rev. 1977, 6, 1-24.
- (1977) Chem. Soc. Rev. , vol.6 , pp. 1-24
- Kirby, G.W.¹

3
- 0032546129
- For reviews of nitroso Diels-Alder reactions, see: (a) Vogt, P. F.; Miller, M. J. Tetrahedron 1998, 54, 1317-1348. (b). Streith, J.; Defoin, A. Synthesis 1994, 1107-1117. (c) Weinreb, S. M.; Staib, R. R. Tetrahedron 1982, 38, 3087-3128.
- (1998) Tetrahedron , vol.54 , pp. 1317-1348
- Vogt, P.F.¹ Miller, M.J.²

4
- 0028019133
- For reviews of nitroso Diels-Alder reactions, see: (a) Vogt, P. F.; Miller, M. J. Tetrahedron 1998, 54, 1317-1348. (b). Streith, J.; Defoin, A. Synthesis 1994, 1107-1117. (c) Weinreb, S. M.; Staib, R. R. Tetrahedron 1982, 38, 3087-3128.
- (1994) Synthesis , pp. 1107-1117
- Streith, J.¹ Defoin, A.²

5
- 0001184378
- For reviews of nitroso Diels-Alder reactions, see: (a) Vogt, P. F.; Miller, M. J. Tetrahedron 1998, 54, 1317-1348. (b). Streith, J.; Defoin, A. Synthesis 1994, 1107-1117. (c) Weinreb, S. M.; Staib, R. R. Tetrahedron 1982, 38, 3087-3128.
- (1982) Tetrahedron , vol.38 , pp. 3087-3128
- Weinreb, S.M.¹ Staib, R.R.²

6
- 0034679048
- For representative examples, see: (a) Abe, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2000, 122, 4583-4592. (b) Carbanal-Duvillard, I.; Berrien, J. F.; Royer, J. Tetrahedron: Asymmetry 2000, 12, 2525-2532. (c) Zhang, D.; Miller, M. J. J. Org. Chem. 1998, 63, 755-759. (c) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602-4611. (d) Ledford, B. E.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 11811-11812. (e) Kibayashi, C.; Aoyagi, S.; Synlett 1995, 873-879. (f) Trost, B. M.; Van Vranken, D. L. J. Am. Chem. Soc. 1993, 115, 444-458. (g) King, S. B.; Ganem, B. J. Am. Chem. Soc. 1991, 113, 5089-5090.
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 4583-4592
- Abe, H.¹ Aoyagi, S.² Kibayashi, C.³

7
- 0034733629
- For representative examples, see: (a) Abe, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2000, 122, 4583-4592. (b) Carbanal-Duvillard, I.; Berrien, J. F.; Royer, J. Tetrahedron: Asymmetry 2000, 12, 2525-2532. (c) Zhang, D.; Miller, M. J. J. Org. Chem. 1998, 63, 755-759. (c) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602-4611. (d) Ledford, B. E.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 11811-11812. (e) Kibayashi, C.; Aoyagi, S.; Synlett 1995, 873-879. (f) Trost, B. M.; Van Vranken, D. L. J. Am. Chem. Soc. 1993, 115, 444-458. (g) King, S. B.; Ganem, B. J. Am. Chem. Soc. 1991, 113, 5089-5090.
- (2000) Tetrahedron: Asymmetry , vol.12 , pp. 2525-2532
- Carbanal-Duvillard, I.¹ Berrien, J.F.² Royer, J.³

8
- 0032489023
- For representative examples, see: (a) Abe, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2000, 122, 4583-4592. (b) Carbanal-Duvillard, I.; Berrien, J. F.; Royer, J. Tetrahedron: Asymmetry 2000, 12, 2525-2532. (c) Zhang, D.; Miller, M. J. J. Org. Chem. 1998, 63, 755-759. (c) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602-4611. (d) Ledford, B. E.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 11811-11812. (e) Kibayashi, C.; Aoyagi, S.; Synlett 1995, 873-879. (f) Trost, B. M.; Van Vranken, D. L. J. Am. Chem. Soc. 1993, 115, 444-458. (g) King, S. B.; Ganem, B. J. Am. Chem. Soc. 1991, 113, 5089-5090.
- (1998) J. Org. Chem. , vol.63 , pp. 755-759
- Zhang, D.¹ Miller, M.J.²

9
- 0000556633
- For representative examples, see: (a) Abe, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2000, 122, 4583-4592. (b) Carbanal-Duvillard, I.; Berrien, J. F.; Royer, J. Tetrahedron: Asymmetry 2000, 12, 2525-2532. (c) Zhang, D.; Miller, M. J. J. Org. Chem. 1998, 63, 755-759. (c) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602-4611. (d) Ledford, B. E.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 11811-11812. (e) Kibayashi, C.; Aoyagi, S.; Synlett 1995, 873-879. (f) Trost, B. M.; Van Vranken, D. L. J. Am. Chem. Soc. 1993, 115, 444-458. (g) King, S. B.; Ganem, B. J. Am. Chem. Soc. 1991, 113, 5089-5090.
- (1994) J. Org. Chem. , vol.59 , pp. 4602-4611
- Ritter, A.R.¹ Miller, M.J.²

10
- 0028788913
- For representative examples, see: (a) Abe, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2000, 122, 4583-4592. (b) Carbanal-Duvillard, I.; Berrien, J. F.; Royer, J. Tetrahedron: Asymmetry 2000, 12, 2525-2532. (c) Zhang, D.; Miller, M. J. J. Org. Chem. 1998, 63, 755-759. (c) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602-4611. (d) Ledford, B. E.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 11811-11812. (e) Kibayashi, C.; Aoyagi, S.; Synlett 1995, 873-879. (f) Trost, B. M.; Van Vranken, D. L. J. Am. Chem. Soc. 1993, 115, 444-458. (g) King, S. B.; Ganem, B. J. Am. Chem. Soc. 1991, 113, 5089-5090.
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 11811-11812
- Ledford, B.E.¹ Carreira, E.M.²

11
- 77953672534
- For representative examples, see: (a) Abe, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2000, 122, 4583-4592. (b) Carbanal-Duvillard, I.; Berrien, J. F.; Royer, J. Tetrahedron: Asymmetry 2000, 12, 2525-2532. (c) Zhang, D.; Miller, M. J. J. Org. Chem. 1998, 63, 755-759. (c) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602-4611. (d) Ledford, B. E.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 11811-11812. (e) Kibayashi, C.; Aoyagi, S.; Synlett 1995, 873-879. (f) Trost, B. M.; Van Vranken, D. L. J. Am. Chem. Soc. 1993, 115, 444-458. (g) King, S. B.; Ganem, B. J. Am. Chem. Soc. 1991, 113, 5089-5090.
- (1995) Synlett , pp. 873-879
- Kibayashi, C.¹ Aoyagi, S.²

12
- 0347584753
- For representative examples, see: (a) Abe, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2000, 122, 4583-4592. (b) Carbanal-Duvillard, I.; Berrien, J. F.; Royer, J. Tetrahedron: Asymmetry 2000, 12, 2525-2532. (c) Zhang, D.; Miller, M. J. J. Org. Chem. 1998, 63, 755-759. (c) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602-4611. (d) Ledford, B. E.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 11811-11812. (e) Kibayashi, C.; Aoyagi, S.; Synlett 1995, 873-879. (f) Trost, B. M.; Van Vranken, D. L. J. Am. Chem. Soc. 1993, 115, 444-458. (g) King, S. B.; Ganem, B. J. Am. Chem. Soc. 1991, 113, 5089-5090.
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 444-458
- Trost, B.M.¹ Van Vranken, D.L.²

13
- 0025880543
- For representative examples, see: (a) Abe, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2000, 122, 4583-4592. (b) Carbanal-Duvillard, I.; Berrien, J. F.; Royer, J. Tetrahedron: Asymmetry 2000, 12, 2525-2532. (c) Zhang, D.; Miller, M. J. J. Org. Chem. 1998, 63, 755-759. (c) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602-4611. (d) Ledford, B. E.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 11811-11812. (e) Kibayashi, C.; Aoyagi, S.; Synlett 1995, 873-879. (f) Trost, B. M.; Van Vranken, D. L. J. Am. Chem. Soc. 1993, 115, 444-458. (g) King, S. B.; Ganem, B. J. Am. Chem. Soc. 1991, 113, 5089-5090.
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 5089-5090
- King, S.B.¹ Ganem, B.²

14
- 37049094978
- Gilchrist, T. L.; Harris, C. J.; Hawkins, D. G.; Moody, C. J.; Rees, C. W. J. Chem. Soc., Perkin Trans. 1 1976, 2166-2715.
- (1976) J. Chem. Soc., Perkin Trans. 1 , pp. 2166-2715
- Gilchrist, T.L.¹ Harris, C.J.² Hawkins, D.G.³ Moody, C.J.⁴ Rees, C.W.⁵

15
- 0001196233
- Zuman, P.; Shah, B. Chem. Rev. 1994, 94, 1621-1641.
- (1994) Chem. Rev. , vol.94 , pp. 1621-1641
- Zuman, P.¹ Shah, B.²

16
- 37049093059
- Horsewood, P. K.; Kirby, G. W. J. Chem. Soc., Perkin Trans. 1980, 1587-1591.
- (1980) J. Chem. Soc., Perkin Trans. , pp. 1587-1591
- Horsewood, P.K.¹ Kirby, G.W.²

17
- 0010700678
- Gilchrist, T. L.; Gonsalves, A. M.; Pinhoe Melo, T. M. V. D. Pure Appl. Chem. 1996, 68, 853-861.
- (1996) Pure Appl. Chem. , vol.68 , pp. 853-861
- Gilchrist, T.L.¹ Gonsalves, A.M.² Pinhoe Melo, T.M.V.D.³

18
- 0344258416
- (a) Ware, R. W.; King, S. B. J. Am. Chem. Soc. 1999, 121, 6769-6770.
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 6769-6770
- Ware, R.W.¹ King, S.B.²

19
- 0034670605
- (b) Ware, R. W.; King, S. B. J. Org. Chem. 2000, 65, 8725-8729.
- (2000) J. Org. Chem. , vol.65 , pp. 8725-8729
- Ware, R.W.¹ King, S.B.²

20
- 0037162752
- (c) Ware, R. W.; King, S. B. J. Org. Chem. 2002, 67, 6174-6180.
- (2002) J. Org. Chem. , vol.67 , pp. 6174-6180
- Ware, R.W.¹ King, S.B.²

21
- 0036775483
- and references therein
- For reviews of guanidine natural products, see: Berlink, R. G. S Nat. Prod. Rep. 2002, 19, 617-649 and references therein.
- (2002) Nat. Prod. Rep. , vol.19 , pp. 617-649
- Berlink, R.G.S.¹

22
- 0035929959
- (a) Batey, R. A.; Powell, D. A. Chem. Commun. 2001, 2362-2363.
- (2001) Chem. Commun. , pp. 2362-2363
- Batey, R.A.¹ Powell, D.A.²

23
- 0012815011
- (b) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913-2916.
- (2002) Org. Lett. , vol.4 , pp. 2913-2916
- Powell, D.A.¹ Batey, R.A.²

24
- 0038003832
- (c) Evindar, G.; Batey, R. A. Org. Lett. 2003, 5, 133-136.
- (2003) Org. Lett. , vol.5 , pp. 133-136
- Evindar, G.¹ Batey, R.A.²

25
- 0037459670
- (d) Powell, D. A.; Ramsden, P. D.; Batey, R. A. J. Org. Chem. 2003, 68, 2300-2309.
- (2003) J. Org. Chem. , vol.68 , pp. 2300-2309
- Powell, D.A.¹ Ramsden, P.D.² Batey, R.A.³

26
- 0000911184
- (a) Yong, Y. Y.; Kowalshi, J. A.; Lipton, M. A. J. Org. Chem. 1997, 62, 1540-1542.
- (1997) J. Org. Chem. , vol.62 , pp. 1540-1542
- Yong, Y.Y.¹ Kowalshi, J.A.² Lipton, M.A.³

27
- 0030936351
- (b) Levallet, C.; Lerpiniere, J.; Ko, S. Y. Tetrahedron 1997, 53, 5291-5304.
- (1997) Tetrahedron , vol.53 , pp. 5291-5304
- Levallet, C.¹ Lerpiniere, J.² Ko, S.Y.³

28
- 0033928301
- (c) Gou, Z.; Cammidge, A.; Horwell, D. C. Synth. Commun. 2000, 30, 2933-2943.
- (2000) Synth. Commun. , vol.30 , pp. 2933-2943
- Gou, Z.¹ Cammidge, A.² Horwell, D.C.³

29
- 0023220536
- Bergeron, R. J.; McManis, J. S. J. Org. Chem. 1987, 52, 1700-1711.
- (1987) J. Org. Chem. , vol.52 , pp. 1700-1711
- Bergeron, R.J.¹ McManis, J.S.²

30
- 1642355829
- For discussion of the term guanylation see ref 11d and references therein
- For discussion of the term guanylation see ref 11d and references therein.

31
- 0037433245
- Until recently no methods existed for the direct observation of acylnitroso species in solution. Time-resolved infrared spectroscopy has recently been employed in the direct detection of acylnitroso compounds in solution. See: Cohen, A. D.; Zeng, B.; King, S. B.; Toscano, J. P. J. Am. Chem. Soc. 2003, 125, 1444-1445.
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 1444-1445
- Cohen, A.D.¹ Zeng, B.² King, S.B.³ Toscano, J.P.⁴

32
- 0018120324
- 4 in water; see: Keck, G. E.; Fleming, S. A. Tetrahedron Lett. 1978, 19, 4763-4766.
- (1978) Tetrahedron Lett. , vol.19 , pp. 4763-4766
- Keck, G.E.¹ Fleming, S.A.²

33
- 1642363998
- note
- 4. The solvent was removed under vacuum, and the resulting product was purified by silica gel chromatography.

34
- 0035958482
- Leach, A. G.; Houk, K. N. J. Org. Chem. 2001, 66, 5192-5200.
- (2001) J. Org. Chem. , vol.66 , pp. 5192-5200
- Leach, A.G.¹ Houk, K.N.²

35
- 0001660954
- Boger, D. L.; Patel, M.; Takusagawa, F. J. Org. Chem. 1985, 50, 1911-1916.
- (1985) J. Org. Chem. , vol.50 , pp. 1911-1916
- Boger, D.L.¹ Patel, M.² Takusagawa, F.³

36
- 0025362839
- Cicchi, S.; Goti, A.; Brandi, A.; Guarna, A.; De Sarlo, F. Tetrahedron Lett. 1990, 31, 3351-3358.
- (1990) Tetrahedron Lett. , vol.31 , pp. 3351-3358
- Cicchi, S.¹ Goti, A.² Brandi, A.³ Guarna, A.⁴ De Sarlo, F.⁵

37
- 0017104078
- Oppolzer, W.; Petrzilka, M. J. Am. Chem. Soc. 1978, 98, 6722-6723.
- (1978) J. Am. Chem. Soc. , vol.98 , pp. 6722-6723
- Oppolzer, W.¹ Petrzilka, M.²

38
- 0001679530
- Shishido, Y.; Kibayashi, C. J. Org. Chem. 1992, 57, 2876-2882.
- (1992) J. Org. Chem. , vol.57 , pp. 2876-2882
- Shishido, Y.¹ Kibayashi, C.²

39
- 0000278587
- Koizumi, T.; Hirai, H.; Yoshii, E. J. Org. Chem. 1982, 47, 4004-4005.
- (1982) J. Org. Chem. , vol.47 , pp. 4004-4005
- Koizumi, T.¹ Hirai, H.² Yoshii, E.³

40
- 0000719026
- Keck, G. E.; Nickell, D. G. J. Am. Chem. Soc. 1980, 102, 3632-3634.
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 3632-3634
- Keck, G.E.¹ Nickell, D.G.²

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