The synthesis of quaternary carbon centers through cyclialkylations

Tetrahedron Letters

Volumn 39, Issue 46, 1998, Pages 8381-8384

  Majetich, George ^a   Fang, Jing ^a  

^a UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; PHENANTHRENE DERIVATIVE;

ALKYLATION; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; REVIEW; SYNTHESIS;

ARENE;

EID: 0032511934     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01931-5     Document Type: Article

References (11)

1. 1. The cyclialkylation of conjugated dienone 11 occurred via two conformers of 11 to produce hydrophenanthrene 12 and naphthalene 13. For a discussion of this study, see: Majetich, G.; Liu, S.; Fang. J.; Siesel, D.; Zhang, Y. J. Org. Chem. 1997, 62, 6928. (formula presented)
2. 2. a) The spectroscopic data obtained for all compounds were consistent with the assigned structures. b) Reaction conditions have not been optimized. c) All yields are isolated yields.
3. 3. a) Delawanna, N. J. J. Org. Chem. 1955, 20, 401.
4. b) Bellamy, F. D.; Du, K. Tetrahedron Lett. 1984, 25, 839.
5. 4. Wender, P. A.; Erhardt, J. M.; Letendre, L. J. Am. Chem. Soc. 1981, 103, 2114.
6. 5. Conjugated 2-aryl-dienones, such as 1, require a cisoid conformation in order to react with the electron-rich arene moiety. The presence of alkyl substituents at C(4) causes a distinct conformational bias towards the cisoid conformation. For a more detailed discussion, see ref. 1.
7. 6. Majetich, G.; Condon, S.; Hull, K.; Ahmad, S. Tetrahedron Lett. 1989, 30, 1033.
8. 7. For the use of Lewis acids, instead of protic ones, to catalyze the dienone-phenol rearrangement, see: a) Chalais, S.; Laszlo, P.; Mathy, A. Tetrahedron Lett. 1986, 27, 2627.
9. For recent examples of this transformation, see: b) Greca, M. D.; Fiorentino, A.; Pinto, G.; Pollio, A.; Previtera, L. J. Org. Chem. 1996, 61, 7178.
10. c) Frimer, A. A.; Marks, V.; Sprecher, M.; Gilinsky-Sharon, P. Ibid. 1994, 59, 1831.
11. 1-5 participation"), followed by ring expansion via a dienone-phenol rearrangement, to generate a tetralin, see: Haddon, V. R.; Jackman, L. M. J. Am. Chem. Soc. 1971, 93, 3832. (formula presented)