-
3
-
-
0000533091
-
-
RajanBabu, T. V.; Nugent, W. A.; Beattie, M. S. J. Am. Chem. Soc. 1990, 112, 6408-6409.
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 6408-6409
-
-
RajanBabu, T.V.1
Nugent, W.A.2
Beattie, M.S.3
-
5
-
-
3543021271
-
-
Marek, I., Ed.; Wiley-VCH: Weinheim; Chapter 12
-
(b) Gansäuer, A.; Rinker, B. In Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, 2002; Chapter 12, pp 435-440.
-
(2002)
Titanium and Zirconium in Organic Synthesis
, pp. 435-440
-
-
Gansäuer, A.1
Rinker, B.2
-
6
-
-
0005208178
-
-
Renaud, P., Sibi, M. P., Eds; Wiley-VCH: Weinheim; Chapter 33
-
(c) Gansäuer, A.; Pierobon, M. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds; Wiley-VCH: Weinheim, 2001; Vol. 2, Chapter 3.3, pp 207-220.
-
(2001)
Radicals in Organic Synthesis
, vol.2
, pp. 207-220
-
-
Gansäuer, A.1
Pierobon, M.2
-
7
-
-
0037041341
-
-
(a) Barrero A. F.; Cuerva, J. M.; Alvarez-Manzaneda, E. J.; Oltra, J. E.; Chahboun, R. Tetrahedron Lett. 2002, 43, 2793-2796.
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 2793-2796
-
-
Barrero, A.F.1
Cuerva, J.M.2
Alvarez-Manzaneda, E.J.3
Oltra, J.E.4
Chahboun, R.5
-
8
-
-
0035356764
-
-
(b) Barrero A. F.; Cuerva, J. M.; Herrador, M. M.; Valdivia, M. V. J. Org. Chem. 2001, 66, 4074-4078.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 4074-4078
-
-
Barrero, A.F.1
Cuerva, J.M.2
Herrador, M.M.3
Valdivia, M.V.4
-
9
-
-
0037134221
-
-
2202
-
Barrero, A. F.; Olatra, J. E.; Cuerva J. M.; Rosales, A. J. Org. Chem. 2202, 67, 2566-2571.
-
J. Org. Chem.
, vol.67
, pp. 2566-2571
-
-
Barrero, A.F.1
Olatra, J.E.2
Cuerva, J.M.3
Rosales, A.4
-
10
-
-
0035968967
-
-
Nakai, K.; Kamoshita, M.; Doi, T.; Yamada, H.; Takahashi, T. Tetrahedron Lett. 2001, 42, 7855-7857.
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 7855-7857
-
-
Nakai, K.1
Kamoshita, M.2
Doi, T.3
Yamada, H.4
Takahashi, T.5
-
11
-
-
0041849812
-
-
Fernández-Mateos, A.; Martín de la Nava, E.; Pascual Coca, G.; Ramos Silvo, A.; Rubio González, R. Org. Lett. 1999, 1, 607-609.
-
(1999)
Org. Lett.
, vol.1
, pp. 607-609
-
-
Fernández-Mateos, A.1
Martín De La Nava, E.2
Pascual Coca, G.3
Ramos Silvo, A.4
Rubio González, R.5
-
12
-
-
0035822901
-
-
A highly selective and efficient isomerization of the epoxide moiety of a dieneoxide (E)-ester to the corresponding exo-methylene allylic dieneol using palladium catalysis has been recently described with occasion of the synthesis of vitamin D fluoro analogues: (a) Kabat, M. M.; Garofalo, L. M.; Daniewski, A. R.; Hutchings, S. D.; Liu, W.; Okabe, M.; Radinov, R.; Zhou, T. J. Org. Chem. 2001, 66, 6141-6150.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 6141-6150
-
-
Kabat, M.M.1
Garofalo, L.M.2
Daniewski, A.R.3
Hutchings, S.D.4
Liu, W.5
Okabe, M.6
Radinov, R.7
Zhou, T.8
-
13
-
-
0037040649
-
-
(b) Daniewski A. R.; Garofalo, L. M.; Hutchings, S. D.; Kabat, M. M.; Liu, W.; Okabe, M.; Radinov, R.; Yiannikouros, G. P. J. Org. Chem. 2002, 67, 1580-1587.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 1580-1587
-
-
Daniewski, A.R.1
Garofalo, L.M.2
Hutchings, S.D.3
Kabat, M.M.4
Liu, W.5
Okabe, M.6
Radinov, R.7
Yiannikouros, G.P.8
-
14
-
-
0000944492
-
-
(a) Baggiolini, E. G.; Iacobelli, J. A.; Hennessy, B. M.; Uskokovic, M. R. J. Am. Chem. Soc. 1982, 104, 2945-2948.
-
(1982)
J. Am. Chem. Soc.
, vol.104
, pp. 2945-2948
-
-
Baggiolini, E.G.1
Iacobelli, J.A.2
Hennessy, B.M.3
Uskokovic, M.R.4
-
15
-
-
0022442161
-
-
(b) Baggiolini, E. G.; Iacobelli, J. A.; Hennessy, B. M.; Batcho, A. D.; Sereno, J. F.; Uskokovic, M. R. J. Org. Chem. 1986, 51, 3098-3108.
-
(1986)
J. Org. Chem.
, vol.51
, pp. 3098-3108
-
-
Baggiolini, E.G.1
Iacobelli, J.A.2
Hennessy, B.M.3
Batcho, A.D.4
Sereno, J.F.5
Uskokovic, M.R.6
-
16
-
-
0037629474
-
-
Molander, G. A.; La Belle, B. E.; Hahn, G. J. Org. Chem. 1986, 51, 5259-5264.
-
(1986)
J. Org. Chem.
, vol.51
, pp. 5259-5264
-
-
Molander, G.A.1
La Belle, B.E.2
Hahn, G.3
-
21
-
-
3543035551
-
-
Experimental procedures for the preparation of 2a-5a, 11a, and 12a are provided in the Supporting Information. Similar transformations have been reported in the enantiomeric series starting from (R)-(-)-carvone: (a) Bermejo, F.; Rico-Ferreira, R.; Bamidele-Sanni, S.; García-Granda, S. J. Org. Chem. 2001, 66, 8257-8260.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 8257-8260
-
-
Bermejo, F.1
Rico-Ferreira, R.2
Bamidele-Sanni, S.3
García-Granda, S.4
-
22
-
-
0032579175
-
-
(b) Rico, R.; Zapico, J.; Bermejo, F. Tetrahedron: Asymmetry 1998, 9, 293-303.
-
(1998)
Tetrahedron: Asymmetry
, vol.9
, pp. 293-303
-
-
Rico, R.1
Zapico, J.2
Bermejo, F.3
-
23
-
-
3543042221
-
-
note
-
2 and fractionation of the reaction mixture by flash chromatography.
-
-
-
-
24
-
-
0024333145
-
-
Hatakeyama, S.; Numata, H.; Shimada, J.; Osanai, K.; Takano, S. J. Org. Chem. 1989, 54, 3515-3517.
-
(1989)
J. Org. Chem.
, vol.54
, pp. 3515-3517
-
-
Hatakeyama, S.1
Numata, H.2
Shimada, J.3
Osanai, K.4
Takano, S.5
-
25
-
-
0040288693
-
-
(a) Roberts, M. R.; Parsons, W. H.; Schlessinger, R. H. J. Org. Chem. 1978, 43, 3970-3972.
-
(1978)
J. Org. Chem.
, vol.43
, pp. 3970-3972
-
-
Roberts, M.R.1
Parsons, W.H.2
Schlessinger, R.H.3
-
28
-
-
3542995422
-
-
note
-
If the titanium chloride attacks the radical (2) from the trans side, the resulting product has the Ti ring group and the acetate in a trans diequatorial conformation (3) that cannot lead to elimination. In order for the latter to occur, the ring would have to flip to a conformation with three axial groups, two of which are strongly eclipsed (4). It is likely that elimination in the direction of the methyl will occur instead in clear contradiction with our results. We are greatly indebted to the reviewer who suggested the cis elimination pathway to us prior to publication of this paper.
-
-
-
-
29
-
-
0000135630
-
-
Paquette, L. A., Ed.; John Wiley & Sons, Inc.: New York
-
Nakai, T.; Mikami, K. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons, Inc.: New York, 1994; Vol. 46, p 105.
-
(1994)
Organic Reactions
, vol.46
, pp. 105
-
-
Nakai, T.1
Mikami, K.2
-
30
-
-
3543012926
-
-
note
-
See the Supporting Information for experimental details on the preparation of epoxides 1a-12a (Table 1).
-
-
-
-
31
-
-
0002714675
-
-
Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925.
-
(1978)
J. Org. Chem.
, vol.43
, pp. 2923-2925
-
-
Still, W.C.1
Kahn, M.2
Mitra, A.3
-
34
-
-
0001059877
-
-
(c) Yasui, K.; Fugami, K.; Tanaka, S.; Tamaru, Y. J. Org. Chem. 1995, 60, 1365-1380.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 1365-1380
-
-
Yasui, K.1
Fugami, K.2
Tanaka, S.3
Tamaru, Y.4
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