-
5
-
-
18844410382
-
-
Y. Gao, R.M. Hanson, J.M. Klunder, S.Y. Ko, H. Masamune, and K.B. Sharpless J. Am. Chem. Soc. 109 1987 5765 5780
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 5765-5780
-
-
Gao, Y.1
Hanson, R.M.2
Klunder, J.M.3
Ko, S.Y.4
Masamune, H.5
Sharpless, K.B.6
-
8
-
-
0002848881
-
-
For representative examples for the reaction of epoxides at the activated carbon having two substituents, see: (a) Y. Naruta, and K. Maruyama Chem. Lett. 1987 963 966
-
(1987)
Chem. Lett.
, pp. 963-966
-
-
Naruta, Y.1
Maruyama, K.2
-
11
-
-
0034966829
-
-
For a recent study on the regioselective ring-opening reaction of chiral epoxides, see: (d) B.D. Brandes, and E.N. Jacobsen Synlett 2001 1013 1015
-
(2001)
Synlett
, pp. 1013-1015
-
-
Brandes, B.D.1
Jacobsen, E.N.2
-
12
-
-
0030981561
-
-
For construction of chiral quaternary carbons, see: (a) R.P. Balasubramaniam, D.K. Moss, J.K. Wyatt, J.D. Spence, A. Gee, and M.H. Nantz Tetrahedron 53 1997 7429 7444
-
(1997)
Tetrahedron
, vol.53
, pp. 7429-7444
-
-
Balasubramaniam, R.P.1
Moss, D.K.2
Wyatt, J.K.3
Spence, J.D.4
Gee, A.5
Nantz, M.H.6
-
24
-
-
0002447983
-
-
K. Okada, T. Katsura, H. Tanino, H. Kakoi, and S. Inoue Chem. Lett. 1994 157 160
-
(1994)
Chem. Lett.
, pp. 157-160
-
-
Okada, K.1
Katsura, T.2
Tanino, H.3
Kakoi, H.4
Inoue, S.5
-
26
-
-
8544276578
-
-
Y. Kita, S. Kitagaki, Y. Yoshida, S. Mihara, D.F. Fang, M. Kondo, S. Okamoto, R. Imai, S. Akai, and H. Fujioka J. Org. Chem. 62 1997 4991 4997
-
(1997)
J. Org. Chem.
, vol.62
, pp. 4991-4997
-
-
Kita, Y.1
Kitagaki, S.2
Yoshida, Y.3
Mihara, S.4
Fang, D.F.5
Kondo, M.6
Okamoto, S.7
Imai, R.8
Akai, S.9
Fujioka, H.10
-
33
-
-
0026100045
-
-
M. Fukumasa, K. Furuhashi, J. Umezawa, O. Takahashi, and T. Hirai Tetrahedron Lett. 32 1991 1059 1062
-
(1991)
Tetrahedron Lett.
, vol.32
, pp. 1059-1062
-
-
Fukumasa, M.1
Furuhashi, K.2
Umezawa, J.3
Takahashi, O.4
Hirai, T.5
-
37
-
-
20444465368
-
-
Ring-opening reaction of epoxides at the more substituted carbon atom with an equimolar amount of a transition metal complex and iodomethane was also reported, see: T. Hase, A. Miyashita, and H. Nohira Chem. Lett. 1988 219 222
-
(1988)
Chem. Lett.
, pp. 219-222
-
-
Hase, T.1
Miyashita, A.2
Nohira, H.3
-
38
-
-
37049085296
-
-
T. Tanaka, T. Inoue, K. Kamei, K. Murakami, and C. Iwata J. Chem. Soc., Chem. Commun. 1990 906 908
-
(1990)
J. Chem. Soc., Chem. Commun.
, pp. 906-908
-
-
Tanaka, T.1
Inoue, T.2
Kamei, K.3
Murakami, K.4
Iwata, C.5
-
39
-
-
0003780608
-
-
Springer Berlin
-
For the epoxide cleavage at the allylic or benzylic position by titanium reagents prepared by chlorotitanium triisopropoxide, see: (a) M.T. Reetz Organotitanium Reagents in Organic Synthesis 1986 Springer Berlin pp 218-219
-
(1986)
Organotitanium Reagents in Organic Synthesis
-
-
Reetz, M.T.1
-
42
-
-
20444441641
-
-
note
-
In some cases, we examined both allylmagnesium chloride and bromide in the ring-opening reaction, and similar results were obtained.
-
-
-
-
43
-
-
20444485439
-
-
note
-
The stereochemistry of 20 is opposite to that of 86 which was obtained by the reaction with allylmagnesium bromide. This stereochemical outcome can be explained by the chelating ability of the titanium reagent to the oxygen atom of the epoxide, which allows the allylation of the ketone from the side of the epoxide oxygen.
-
-
-
-
44
-
-
0001615493
-
-
Stereoselective reactions of cyclic epoxides such as substituted cyclohexene oxides with a titanium reagent were already reported, see Ref. 10b. See also, (a) C. Blandy, R. Choukroun, and D. Gervais Tetrahedron Lett. 24 1983 4189 4192
-
(1983)
Tetrahedron Lett.
, vol.24
, pp. 4189-4192
-
-
Blandy, C.1
Choukroun, R.2
Gervais, D.3
-
55
-
-
0025985752
-
-
M. Canas, M. Poch, X. Verdaguer, A. Moyano, M.A. Pericaǐs, and A. Riera Tetrahedron Lett. 32 1991 6931 6934
-
(1991)
Tetrahedron Lett.
, vol.32
, pp. 6931-6934
-
-
Canas, M.1
Poch, M.2
Verdaguer, X.3
Moyano, A.4
Pericaǐs, M.A.5
Riera, A.6
-
59
-
-
0001713826
-
-
T. Suzuki, H. Saimoto, H. Tomioka, K. Oshima, and H. Nozaki Tetrahedron Lett. 23 1982 3597 3600
-
(1982)
Tetrahedron Lett.
, vol.23
, pp. 3597-3600
-
-
Suzuki, T.1
Saimoto, H.2
Tomioka, H.3
Oshima, K.4
Nozaki, H.5
-
62
-
-
0012550127
-
-
K.H. Ahn, J.S. Kim, C.S. Jin, D.H. Kang, D.S. Han, Y.S. Shin, and D.H. Kim Synlett 1992 306 308
-
(1992)
Synlett
, pp. 306-308
-
-
Ahn, K.H.1
Kim, J.S.2
Jin, C.S.3
Kang, D.H.4
Han, D.S.5
Shin, Y.S.6
Kim, D.H.7
-
66
-
-
0035939140
-
-
R. Martiǐn, G. Islas, A. Moyano, M.A. Pericàs, and A. Riera Tetrahedron 57 2001 6367 6374
-
(2001)
Tetrahedron
, vol.57
, pp. 6367-6374
-
-
Martiǐn, R.1
Islas, G.2
Moyano, A.3
Pericàs, M.A.4
Riera, A.5
-
68
-
-
0038732511
-
-
For a recent theoretical study, see: I. Infante, C. Bonini, F. Lelj, and G. Righi J. Org. Chem. 68 2003 3773 3780
-
(2003)
J. Org. Chem.
, vol.68
, pp. 3773-3780
-
-
Infante, I.1
Bonini, C.2
Lelj, F.3
Righi, G.4
-
69
-
-
20444464958
-
-
note
-
Only a relatively small NOE enhancement was observed between 4-H and the siloxymethyl group.
-
-
-
-
70
-
-
20444456771
-
-
note
-
Halohydrin is one of the representative side products irrespective of the Grignard reagent used, the stereochemistry of which is not determined. No stereo- or regioisomer of the allylated product was detected in the reaction mixture.
-
-
-
-
71
-
-
20444462472
-
-
note
-
Relative stereochemistries of the quaternary carbons were determined by NOE experiment of the corresponding lactones. Typical examples are shown below.
-
-
-
-
72
-
-
20444468978
-
-
note
-
We investigated the titanium-mediated ring-opening reaction of epoxides with benzyl-, crotyl-, or vinylmagnesium halide; however, a complex mixture of unidentified products was obtained in every case.
-
-
-
-
78
-
-
0028263520
-
-
Y. Kotake, A. Iijima, K. Yoshimatsu, N. Tamai, Y. Ozawa, N. Koyanagi, K. Kitoh, and H. Nomura J. Med. Chem. 37 1994 1616 1624
-
(1994)
J. Med. Chem.
, vol.37
, pp. 1616-1624
-
-
Kotake, Y.1
Iijima, A.2
Yoshimatsu, K.3
Tamai, N.4
Ozawa, Y.5
Koyanagi, N.6
Kitoh, K.7
Nomura, H.8
-
79
-
-
0028953858
-
-
M. Kimura, P.V. Diwan, S. Yanagi, Y. Kon-no, H. Nojima, and I. Kimura Biol. Pharm. Bull. 18 1995 407 410
-
(1995)
Biol. Pharm. Bull.
, vol.18
, pp. 407-410
-
-
Kimura, M.1
Diwan, P.V.2
Yanagi, S.3
Kon-No, Y.4
Nojima, H.5
Kimura, I.6
-
85
-
-
0028142743
-
-
C.M. Rodriǐguez, T. Martiǐn, M.A. Ramiǐrez, and V.S. Martiǐn J. Org. Chem., 59 1994 4461 4472
-
(1994)
J. Org. Chem.
, vol.59
, pp. 4461-4472
-
-
Rodriǐguez, C.M.1
Martiǐn, T.2
Ramiǐrez, M.A.3
Martiǐn, V.S.4
|