Novel reductive olefination mediated by Ti(O-i-Pr)4 and Ph3P. One-pot synthesis of trifluoromethylated trans-allylic alcohols
(Note: The full text of this document is currently only available in the PDF Version )
Yanchang Shen, Yuming Zhang and Yuefen Zhou
Abstract
A novel reductive olefination mediated by Ti(O-i-Pr)4 and Ph3P and its application to the ‘one-pot’ synthesis of perfluoroalkylated trans-allylic alcohols are described.
References
L. F. Tietze and U. Beifuss, Angew. Chem., Int. Ed. Engl., 1993, 32, 131 CrossRef; L. F. Tietze, Chem. Rev., 1996, 96, 115 CrossRefCAS.
Y. Shen, Acc. Chem. Res., 1998, 31CrossRef in press.
W. F. Berkowitz and A. S. Amarasekara, Tetrahedron Lett., 1985, 26, 3663 CrossRefCAS; Y. Tamura, H. Annoura and H. Fujioka, Tetrahedron Lett., 1987, 28, 5681 CrossRefCAS; C. Singh, Tetrahedron Lett., 1990, 31, 6901 CrossRefCAS; J. Barluenga, L. Llavona, P. L. Bernad and J. M. Concellon, Tetrahedron Lett., 1993, 34, 3173 CrossRefCAS and refs. cited therein.
N. Ono, A. Kamimura and A. Kaji, Tetrahedron Lett., 1984, 25, 5319 CrossRefCAS; H. Jin, J. Uenishi, W. J. Christ and Y. Kishi, J. Am. Chem. Soc., 1986, 108, 5644 CrossRefCAS; K. Takai, M. Tagashira, T. Kuroda, K. Oshima, K. Utimoto and H. Nozaki, J. Am. Chem. Soc., 1986, 108, 6048 CrossRefCAS; M. Srebnik, Tetrahedron Lett., 1991, 32, 2449 CrossRefCAS; J. C. Fuller, E. L. Stangeland, C. T. Goralski and B. Singaram, Tetrahedron Lett., 1993, 34, 257 CrossRefCAS; V. A. Khripach, V. N. Zhabinskii and E. V. Zhernosek, Tetrahedron Lett., 1995, 36, 607 CrossRefCAS.
E. Oblinger and J. Montgomery, J. Am. Chem. Soc., 1997, 119, 9065 CrossRefCAS.
(a) N. Ishikawa, M. G. Koh, T. Kitazume and S. K. Choi, J. Fluorine Chem., 1984, 24, 419 CrossRefCAS;
(b) Y. Shen and T. Wang, Tetrahedron Lett., 1989, 30, 7203 CrossRefCAS;
(c) T. Kitazume, J. T. Lin and T. Yamazaki, J. Fluorine Chem., 1989, 43, 177 CrossRefCAS;
(d) T. Kubota and M. Yamamoto, Tetrahedron Lett., 1992, 33, 2603 CrossRefCAS;
(e) K. Funabiki, Y. Fukushima, T. Inagaki, E. Murata, M. Matsui and K. Shibata, Tetrahedron Lett., 1998, 39, 1913 CrossRefCAS;
(f) M. J. Broadhurst, J. M. Percy and M. E. Prime, Tetrahedron Lett., 1997, 38, 5903 CrossRefCAS;
(g) F. Tellier, M. Baudry and R. Sauvetre, Tetrahedron Lett., 1997, 38, 5989 CrossRefCAS;
(h) M. Omote, A. Ando, T. Takagi, M. Koyama and I. Kumadaki, Heterocycles, 1997, 44, 89 CAS.
J. March,
Advanced Organic Chemistry,
4th edn., John Wiley & Sons,
New York,
1992,
p. 917 Search PubMed.
R. K. Mackie,
in Organophosphorus Reagents in Organic Synthesis,
ed. J. I. G. Cadogen,
Academic Press,
London,
1979,
p.542 Search PubMed.
Y. Shen and B. Yang, J. Organomet. Chem., 1989, 375, 45 CrossRefCAS.
After fractional distillation under vacuum, a colorless oil 4 was obtained which was sensitive to moisture. Bp 110 °C/0.1 torr;
δH(300 MHz, CDCl3, TMS) 5.00–4.20 (m, 4H), 3.58 [dd, 2J(H,H) 10.9,
3J(H,H) 3.2, 1H], 3.10 [dd, 2J(H,H) 10.6, 3J(H,H) 8.8, 1H], 1.28 [d,
3J(H,H) 6.1, 18H]; δF(60 MHz, CDCl3, TFA) 0.3 [d, 3J(H,F) 5.4].
Click here to see how this site uses Cookies. View our privacy policy here.