Diastereoselective generation of lithium carbenoid reagent RCH(OMEM)CFBrLi and its reaction with electrophiles

Tetrahedron Letters

Volumn 37, Issue 41, 1996, Pages 7387-7390

  Shimizu, Masaki ^a   Takebe, Yoko ^a   Kuroboshi, Manabu ^a,b   Hiyama, Tamejiro ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOFLUORINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030574035     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01684-X     Document Type: Article

References (15)

1. 1. Reviews: (a) Welch, J. T. Tetrahedron 1987, 43, 3123-3197.
2. (b) Organofluorine Chemistry. Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds,; Plenum Press, New York, 1994.
3. (c) Chemistry of Organic Fluorine Compounds II. A Critical Review; Hudlicky, M.; Pavlath, A. E., Eds.; ACS Monograph 187; American Chemical Society: Washington, DC, 1995.
4. 2. Reviews: (a) Burton, D. J.; Yang, Z.-Y. Tetrahedron 1992, 48, 189-275.
5. (b) Burton, D. J.; Yang, Z.-Y.; Morken, P. A. Tetrahedron 1994, 50, 2993-3063.
6. 3. (a) Kuroboshi, M.; Yamada, N.; Takebe, Y.; Hiyama, T. Synlett 1995, 987-988.
7. (b) Kuroboshi, M.; Yamada, N.; Takebe, Y.; Hiyama, T. Tetrahedron Lett. 1995, 36, 6271-6274.
8. 4. Review: Takeuchi, Y. Yuki Gosei Kagaku Kyokai Shi 1988, 46, 145-159.
9. 5. Hoffmann et al. studied the diastereoselective bromine-lithium exchange of 3-alkoxy-1, 1-dibromoalkanes extensively, but 1,1-dibromo-3-methyl-2-(trimethylsilyloxy)butane was tested only for diastereoselective generation of β-alkoxy-α-bromoalkyllithium. (a) Hoffmann, R. W.; Stiasny, H. C.; Kruger J. Tetrahedron 1996, 52, 7421-7434.
10. (b) Hoffmann, R. W.; Julius, M. Liebigs Ann. Chem. 1991, 811-822 and references cited therein.
11. H-F of the acetonides prepared through deprotection followed by acetalization. (formula presented)
12. 7. When OR' was OAc or F, only β-elimination reaction occurred, giving rise to 1-bromo-1-fluoro-2-(1-naphthyl)ethene in good yields (E : Z = 2 : 1).
13. 8. Ishihara, T.; Ichihara, K.; Yamanaka, H. Tetrahedron Lett. 1995, 36, 8267-8270.
14. 9. Conformations involving the interaction between lithium and fluorine also may be possible, but this model does not explain the size effect of the substituent. For the interaction between lithium and fluorine, see Yamazaki, T.; Shinohara, N.; Kitazume, T.; Sato, S. J. Org. Chem. 1995, 60, 8140-8141 and references cited therein.
15. 3) δ 4.14 (ddd, J = 4.3, 5.9, 12.2 Hz, 1H) for syn-8 (lit. 4.23 (dd, J = 2.5, 7.0 Hz), 4.03 (m, 1H) for anti-8 (lit. 4.10 (brs, 1H).