Mitsunobu-type alkylation of p-toluenesulfonamide. A convenient new route to primary and secondary amines

Tetrahedron Letters

Volumn 37, Issue 14, 1996, Pages 2457-2458

  Tsunoda, Tetsuto ^a   Yamamoto, Hidetoshi ^a   Goda, Kayo ^a   Itô, Shô ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029879822     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00317-6     Document Type: Article

References (12)

1. Reviews: Hughes, D. L. The Mitsunobu Reactions, in Organic Reactions; Beak, P. et al. Eds; John Wiley & Sons, Inc.: New York, 1992, Vol. 42, pp 335-656. Recent works: e.g. Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373-6374. Bell, K.-E.; Knight, D.-W.; Gravestock, M.-B. Tetrahedron Lett. 1995, 36, 8681-8684, and the references cited therein.
2. Reviews: Hughes, D. L. The Mitsunobu Reactions, in Organic Reactions; Beak, P. et al. Eds; John Wiley & Sons, Inc.: New York, 1992, Vol. 42, pp 335-656. Recent works: e.g. Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373-6374. Bell, K.-E.; Knight, D.-W.; Gravestock, M.-B. Tetrahedron Lett. 1995, 36, 8681-8684, and the references cited therein.
3. Reviews: Hughes, D. L. The Mitsunobu Reactions, in Organic Reactions; Beak, P. et al. Eds; John Wiley & Sons, Inc.: New York, 1992, Vol. 42, pp 335-656. Recent works: e.g. Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373-6374. Bell, K.-E.; Knight, D.-W.; Gravestock, M.-B. Tetrahedron Lett. 1995, 36, 8681-8684, and the references cited therein.
4. Interal., Na / naphthalene: Ji, S.; Gortler, L. B.; Waring, A.; Battisti, A.; Bank, S.; Closson, W. D.; Wriede, P. J. Am. Chem. Soc. 1967, 89, 5311-5312. Na / ammonia: Kovacs, J.; Ghatak, U. R. J. Org. Chem. 1966, 31, 119-121.
5. Interal., Na / naphthalene: Ji, S.; Gortler, L. B.; Waring, A.; Battisti, A.; Bank, S.; Closson, W. D.; Wriede, P. J. Am. Chem. Soc. 1967, 89, 5311-5312. Na / ammonia: Kovacs, J.; Ghatak, U. R. J. Org. Chem. 1966, 31, 119-121.
6. Bittner, S.; Assaf, Y.; Krief, P.; Pomerantz, M.; Ziemnicka, B.T.; Smith, C. G. J. Org. Chem. 1985, 50, 1712-1718.
7. Tsunoda, T.; Yamamiya, Y.; Itô, S. Tetrahedron Lett. 1993, 34, 1639-1642. Tsunoda, T.; Otsuka, J.; Yamamiya, Y.; Itô, S. Chemistry Lett. 1994, 539-542. Itô, S.; Tsunoda, T. Pure & Appl. Chem. 1994, 66, 2071-2074. Tsunoda, T.; Nagaku, M.; Nagino, C.; Kawamura, Y.; Ozaki, F.; Hioki, H.; Itô, S. Tetrahedron Lett. 1995, 36, 2531-2534.
8. Tsunoda, T.; Yamamiya, Y.; Itô, S. Tetrahedron Lett. 1993, 34, 1639-1642. Tsunoda, T.; Otsuka, J.; Yamamiya, Y.; Itô, S. Chemistry Lett. 1994, 539-542. Itô, S.; Tsunoda, T. Pure & Appl. Chem. 1994, 66, 2071-2074. Tsunoda, T.; Nagaku, M.; Nagino, C.; Kawamura, Y.; Ozaki, F.; Hioki, H.; Itô, S. Tetrahedron Lett. 1995, 36, 2531-2534.
9. Tsunoda, T.; Yamamiya, Y.; Itô, S. Tetrahedron Lett. 1993, 34, 1639-1642. Tsunoda, T.; Otsuka, J.; Yamamiya, Y.; Itô, S. Chemistry Lett. 1994, 539-542. Itô, S.; Tsunoda, T. Pure & Appl. Chem. 1994, 66, 2071-2074. Tsunoda, T.; Nagaku, M.; Nagino, C.; Kawamura, Y.; Ozaki, F.; Hioki, H.; Itô, S. Tetrahedron Lett. 1995, 36, 2531-2534.
10. Tsunoda, T.; Yamamiya, Y.; Itô, S. Tetrahedron Lett. 1993, 34, 1639-1642. Tsunoda, T.; Otsuka, J.; Yamamiya, Y.; Itô, S. Chemistry Lett. 1994, 539-542. Itô, S.; Tsunoda, T. Pure & Appl. Chem. 1994, 66, 2071-2074. Tsunoda, T.; Nagaku, M.; Nagino, C.; Kawamura, Y.; Ozaki, F.; Hioki, H.; Itô, S. Tetrahedron Lett. 1995, 36, 2531-2534.
11. Tsunoda, T.; Ozaki, F.; Itô, S. Tetrahedron Lett. 1994, 35, 5081-5082.
12. The amine 8 is one of the squalene synthetase inhibitors, and 10 is the tosyl derivative of another. Cf. Prashad, M.; Kathawala, F. J.; Scallen, T. J. Med. Chem. 1993, 36, 1501-1504.