Efficient entry to tetrahydropyridines: Addition of enol ethers to allenesulfonamides involving a novel 1,3-sulfonyl shift

Angewandte Chemie - International Edition

Volumn 38, Issue 1-2, 1999, Pages 121-124

  Horino, Yoshikazu ^a   Kimura, Masanari ^a   Wakamiya, Yoshinori ^a   Okajima, Toshiya ^b   Tamaru, Yoshinao ^a  

^a NAGASAKI UNIVERSITY   (Japan)

^b SAGA UNIVERSITY   (Japan)

Author keywords

1,3 sulfonyl shift; Allenes; Cyclizations; Oxazolidinones; Tetrahydropyridines

Indexed keywords

ALLENESULFONAMIDE; PYRIDINE DERIVATIVE; TETRAHYDROPYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONJUGATION; CYCLIZATION; ELECTRON TRANSPORT; ISOMERISM; ORGANIC CHEMISTRY; REACTION ANALYSIS; SPECTROSCOPY;

EID: 0033555653     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990115)38:1/2<121::AID-ANIE121>3.0.CO;2-D     Document Type: Article

References (41)

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24. Similar coupling patterns and nOes were observed for cis-3f and cis-3i. See the Experimental Section for the characteristic coupling patterns that trans-3 displays.
25. A radical mechanism involving homolytic N-S bond cleavage may be ruled out based on the fact that methanesulfonamide 1c (run 10, Table 1) shows reaction features similar to those of toluenesulfonamides 1a, b: B. Quiclet-Sirc. S. Z. Zard, J. Am. Chem. Soc. 1996, 118, 1209-1210; S. Kim, J.-Y. Yoon, J. Am. Chem. Soc. 1997, 119, 5982-5983, and references therein.
26. A radical mechanism involving homolytic N-S bond cleavage may be ruled out based on the fact that methanesulfonamide 1c (run 10, Table 1) shows reaction features similar to those of toluenesulfonamides 1a, b: B. Quiclet-Sirc. S. Z. Zard, J. Am. Chem. Soc. 1996, 118, 1209-1210; S. Kim, J.-Y. Yoon, J. Am. Chem. Soc. 1997, 119, 5982-5983, and references therein.
27. A similar four-membered cyclic transition state has been proposed for the 1,3-shift of chlorine in chlorocarbonylketene: J. Finnerty, J. Andraos, Y. Yamamoto, M. W. Wong, C. Wentrup, J. Am. Chem. Soc. 1998, 120, 1701-1704.: see also H. Binas, M. W. Wong, C. Wentrup, Chem. Eur. J. 1997, 31, 237-248, and references therein.
28. A similar four-membered cyclic transition state has been proposed for the 1,3-shift of chlorine in chlorocarbonylketene: J. Finnerty, J. Andraos, Y. Yamamoto, M. W. Wong, C. Wentrup, J. Am. Chem. Soc. 1998, 120, 1701-1704.: see also H. Binas, M. W. Wong, C. Wentrup, Chem. Eur. J. 1997, 31, 237-248, and references therein.
29. 2 bond cleavage: S. M. Weinreb, D. M. Demko, T. A. Lessen, Tetrahedron Lett. 1986, 27. 2099-2102; T. Fukuyama, C.-K. Jow, M. Cheung, Tetrahedron Lett. 1995, 36, 6373-6374; C. Huart, L. Ghosez, Angew. Chem. 1997, 109, 627-629; Angew. Chem. Int. Ed. Engl. 1997, 36, 634-636.
30. 2 bond cleavage: S. M. Weinreb, D. M. Demko, T. A. Lessen, Tetrahedron Lett. 1986, 27. 2099-2102; T. Fukuyama, C.-K. Jow, M. Cheung, Tetrahedron Lett. 1995, 36, 6373-6374; C. Huart, L. Ghosez, Angew. Chem. 1997, 109, 627-629; Angew. Chem. Int. Ed. Engl. 1997, 36, 634-636.
31. 2 bond cleavage: S. M. Weinreb, D. M. Demko, T. A. Lessen, Tetrahedron Lett. 1986, 27. 2099-2102; T. Fukuyama, C.-K. Jow, M. Cheung, Tetrahedron Lett. 1995, 36, 6373-6374; C. Huart, L. Ghosez, Angew. Chem. 1997, 109, 627-629; Angew. Chem. Int. Ed. Engl. 1997, 36, 634-636.
32. 2 bond cleavage: S. M. Weinreb, D. M. Demko, T. A. Lessen, Tetrahedron Lett. 1986, 27. 2099-2102; T. Fukuyama, C.-K. Jow, M. Cheung, Tetrahedron Lett. 1995, 36, 6373-6374; C. Huart, L. Ghosez, Angew. Chem. 1997, 109, 627-629; Angew. Chem. Int. Ed. Engl. 1997, 36, 634-636.
33. 2 bond cleavage: S. M. Weinreb, D. M. Demko, T. A. Lessen, Tetrahedron Lett. 1986, 27. 2099-2102; T. Fukuyama, C.-K. Jow, M. Cheung, Tetrahedron Lett. 1995, 36, 6373-6374; C. Huart, L. Ghosez, Angew. Chem. 1997, 109, 627-629; Angew. Chem. Int. Ed. Engl. 1997, 36, 634-636.
34. 2 bond cleavage: S. M. Weinreb, D. M. Demko, T. A. Lessen, Tetrahedron Lett. 1986, 27. 2099-2102; T. Fukuyama, C.-K. Jow, M. Cheung, Tetrahedron Lett. 1995, 36, 6373-6374; C. Huart, L. Ghosez, Angew. Chem. 1997, 109, 627-629; Angew. Chem. Int. Ed. Engl. 1997, 36, 634-636.
35. 2 bond cleavage: S. M. Weinreb, D. M. Demko, T. A. Lessen, Tetrahedron Lett. 1986, 27. 2099-2102; T. Fukuyama, C.-K. Jow, M. Cheung, Tetrahedron Lett. 1995, 36, 6373-6374; C. Huart, L. Ghosez, Angew. Chem. 1997, 109, 627-629; Angew. Chem. Int. Ed. Engl. 1997, 36, 634-636.
36. Thiophene failed to react with 1a to furnish 3. Instead, 4-vinyl-4-oxazolin-2-one (product of a 1,3-hydrogen shift) was provided in 88% yield (1a/thiophene = 1/100 mol/mol. 80 C. 11 h).
37. 1H NMR spectroscopy and HPLC. There were only very small amounts of impurities; 20, 29, and 51% conversions after 2,4, and 9 h at 70 C, respectively.
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41. We thank the referee who pointed out the possibility that 3g might be formed by the Diels - Alder addition of turan (4π) and the vinyl group of 5 and subsequent 1-aza-Cope rearrangement.