Mitsunobu-type alkylation with active methine compounds

Tetrahedron Letters

Volumn 37, Issue 14, 1996, Pages 2459-2462

  Tsunoda, Tetsuto ^a   Nagino, Chisato ^a   Oguri, Miwa ^a   Itô, Shô ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANE DERIVATIVE; SULFONIC ACID DERIVATIVE; SULFOXIDE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029967484     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00318-8     Document Type: Article

References (13)

1. Reviews: Mitsunobu, O. Synthesis 1981, 1-28. Hughes, D. L. The Mitsunobu Reaction, in Organic Reactions; Beak, P. et al. Eds; John Wiley & Sons, Inc.: New York, 1992, Vol. 42, pp 335-656.
2. Reviews: Mitsunobu, O. Synthesis 1981, 1-28. Hughes, D. L. The Mitsunobu Reaction, in Organic Reactions; Beak, P. et al. Eds; John Wiley & Sons, Inc.: New York, 1992, Vol. 42, pp 335-656.
3. 3 mediated alkylation of bis(phenylsulfonyl)methane and its derivatives in good to excellent yields (Yu, J.; Cho, H.-S.; Falck, J. R. J. Org. Chem. 1993, 58, 5892-5894, Yu, J.; Cho, H.-S.; Falck, J. R. Tetrahedron Lett. 1995, 36, 8577-8580).
4. 3 mediated alkylation of bis(phenylsulfonyl)methane and its derivatives in good to excellent yields (Yu, J.; Cho, H.-S.; Falck, J. R. J. Org. Chem. 1993, 58, 5892-5894, Yu, J.; Cho, H.-S.; Falck, J. R. Tetrahedron Lett. 1995, 36, 8577-8580).
5. a. Tsunoda, T.; Nagaku, M.; Nagino, C.; Kawamura, Y.; Ozaki, F.; Hioki, H.; Itô, S. Tetrahedron Lett. 1995, 36, 2531-2534.
6. b. Tsunoda, T.; Yamamiya, Y.; Itô, S. Tetrahedron Lett. 1993, 34, 1639-1642.
7. c. Tsunoda, T.; Otsuka, J.; Yamamiya, Y.; Itô, S. Chemistry Lett. 1994, 539-542.
8. Tsunoda, T.; Ozaki, F.; Itô, S. Tetrahedron Lett. 1994, 35, 5081-5082.
9. Lai, J-Y.; Yu, J.; Hawkins, R. D.; Falck, J. R. Tetrahedron Lett. 1995, 36, 5691-5694.
10. 1H-NMR: δ 1.03 (1H, s), 1.64 (9H, d, J = 12.8). Very sensitive to air. All procedures for the preparation and purification of CMMP as well as its reactions should be carried out under strictly dry argon atmosphere. (formula presented)
11. 3c
12. 5 was confirmed in the reaction of 2a with 2-octanol to give the alkylation product in 0% and 54% yield, respectively. Compare the values with those in entry 2 in Table 1.
13. 1H-NMR , and mass spectra.