Hydroxyl-directed reductive ring opening at the C-2 position of functionalized 2-aryloxetanes

Tetrahedron Letters

Volumn 37, Issue 25, 1996, Pages 4363-4364

  Bach, Thorsten ^a   Lange, Christian ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYL GROUP; OXETANE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REDUCTION; STEREOCHEMISTRY;

ARENE;

EID: 0029991508     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00781-2     Document Type: Article

References (15)

1. (a) Searles, S. in The Chemistry of Heterocyclic Compounds (Ed.: A. Weissberger), Wiley-Interscience New York, 1964, vol. 19-2, pp. 983-1068.
2. (b) Searles, S. in Comprehensive Heterocyclic Chemistry (Ed.: A. R. Katritzky), Pergamon Press, Oxford 1984, vol. 7, pp. 363-402.
3. Recent review about the Paternò-Büchi reaction: Mattay, J.; Conrads, R.; Hoffmann, R. in Methoden der Organischen Chemie (Houben-Weyl) 4te Aufl., vol. E 21c, (Eds.: Helmchen, G.; Hoffmann, R.W.; Mulzer, J.; Schaumann, E.); Thieme, Stuttgart 1995, pp. 3133-3178.
4. (a) Bach, T.; Jödicke, K. Chem. Ber. 1993, 126, 2457-2466.
5. (b) Bach, T. Liebigs. Ann. 1995, 855-866, and refs. cited therein.
6. (a) Bach, T. Tetrahedron Lett. 1994, 35, 1855-1858.
7. (b) Bach, T. Liebigs. Ann. 1995, 1045-1053.
8. (a) Searles Jr., S.; Pollart, K.A.; Lutz, E.F. J. Am. Chem. Soc. 1957, 19 , 948-951.
9. (b) Seyden-Penne, J.; Schaal, C. Bull. Soc. Chim. Fr. 1969 , 3653-3654.
10. (c) Ruotsalainen, H.; Palosaari, V.; Olavi I., P. Suom. Kemistilehti B 1972, 45, 40-42.
11. (d) Krishnamurthy, S.; Brown, H.C. J. Org. Chem. 1979, 44, 3678-3682.
12. (e) Bach, T.; Kather, K. J. Org. Chem. 1996, 61, in print.
13. Bach, T.; Kather, K. Tetrahedron 1994, 50, 12319-12328.
14. Taylor, E.C.; McLay, G.W.; McKillop, A. J. Am. Chem. Soc. 1968, 90, 2422-2423.
15. 3) for some representative examples 4a: δ = 1.00 (d, J = 6.9 Hz, 6 H), 1.89 (sept, J = 6.9 Hz, 1 H), 2.66 (d, J = 14.6 Hz1 1 H), 2.97 (d, J = 14.6 Hz, 1 H), 3.39 (d, J = 11.2 Hz, 1 H), 3.57 (d, J = 11.2Hz, 1 H), 6.87-7.18 (m, 4 H). 4d: δ = 2.84 (s, 2 H), 3.42 (d, J = 11.6 Hz, 1 H), 3.50 (s, 3 H), 3.55 (s, 3 H), 3.82 (d, J = 11.6 Hz, 1 H), 4.13 (s, 1 H) 6.82-7.20 (m, 4 H). 4f: δ = 1.19 (s, 6 H), 2.61 (d, J = 14.5Hz, 1 H), 3.22 (d, J = 14.5 Hz, 1 H), 3.58 (d, J = 11.9 Hz, 1 H), 3.65 (d, J = 11.9 Hz, 1 H), 5.12-5.18 (m, 2 H), 6.11 -6.22 (m, 1 H), 6.81 -7.18 (m, 4 H).