-
1
-
-
0037944068
-
-
and pertinent references cited therein
-
For a recent review on the palladium assisted construction of nucleosides, see: L. A. Agrofoglio, I. Gillaizeau and Y. Saito, Chem. Rev., 2003, 103, 1875 and pertinent references cited therein.
-
(2003)
Chem. Rev.
, vol.103
, pp. 1875
-
-
Agrofoglio, L.A.1
Gillaizeau, I.2
Saito, Y.3
-
2
-
-
4243987144
-
-
and pertinent references therein
-
For a review on allylic animation, see: M. Johannsen and K. A. Jørgensen, Chem. Rev., 1998, 98, 1689 and pertinent references therein.
-
(1998)
Chem. Rev.
, vol.98
, pp. 1689
-
-
Johannsen, M.1
Jørgensen, K.A.2
-
3
-
-
4344566130
-
-
and pertinent references cited therein
-
For a recent perspective of asymmetric allylic substitution, in which nucleosides are utilized as nucleophiles, see: B. M. Trost, J. Org. Chem., 2004, 69, 5813 and pertinent references cited therein.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 5813
-
-
Trost, B.M.1
-
4
-
-
0003692824
-
-
For an example of the challenges associated with controlling regioselectivity in the metal-catalyzed allylic amination of unsymmetrical allylic alcohol derivatives using nucleosides, see: M. L. Falck-Pedersen, T. Benneche and K. Undheim, Acta Chem. Scand., 1989, 43, 251.
-
(1989)
Acta Chem. Scand.
, vol.43
, pp. 251
-
-
Falck-Pedersen, M.L.1
Benneche, T.2
Undheim, K.3
-
5
-
-
0041419939
-
-
(a) C. Anastasi, G. Quéléver, S. Burlet, C. Garino, F. Souard and J.-L. Kraus, Curr. Med. Chem., 2003, 10, 1825;
-
(2003)
Curr. Med. Chem.
, vol.10
, pp. 1825
-
-
Anastasi, C.1
Quéléver, G.2
Burlet, S.3
Garino, C.4
Souard, F.5
Kraus, J.-L.6
-
6
-
-
0345688175
-
-
and pertinent references cited therein
-
(b) V. L. Damaraju, S. Damaraju, J. D. Young, S. A. Baldwin, J. Mackey, M. B. Sawyer and C. E. Cass, Oncogene, 2003, 22, 7524 and pertinent references cited therein.
-
(2003)
Oncogene
, vol.22
, pp. 7524
-
-
Damaraju, V.L.1
Damaraju, S.2
Young, J.D.3
Baldwin, S.A.4
Mackey, J.5
Sawyer, M.B.6
Cass, C.E.7
-
7
-
-
0035829460
-
-
For a few representative examples of biologically important carbanucleosides, see: (a) G. Y. Song, V. Paul, H. Choo, J. Morrey, R. W. Sidwell, R. F. Schinazi and C. K. Chu, J. Med Chem., 2001, 44, 3985;
-
(2001)
J. Med. Chem.
, vol.44
, pp. 3985
-
-
Song, G.Y.1
Paul, V.2
Choo, H.3
Morrey, J.4
Sidwell, R.W.5
Schinazi, R.F.6
Chu, C.K.7
-
8
-
-
0037479917
-
-
(b) Y. Choi, C. George, M. J. Comin, J. J. Barchi Jr., H. S. Kim, K. A. Jacobson, J. Balzarini, H. Mitsuya, P. L. Boyer, S. H. Hughes and V. E. Marquez, J. Med Chem., 2003, 46, 3292;
-
(2003)
J. Med. Chem.
, vol.46
, pp. 3292
-
-
Choi, Y.1
George, C.2
Comin, M.J.3
Barchi Jr., J.J.4
Kim, H.S.5
Jacobson, K.A.6
Balzarini, J.7
Mitsuya, H.8
Boyer, P.L.9
Hughes, S.H.10
Marquez, V.E.11
-
9
-
-
12344254832
-
-
and pertinent references cited therein
-
(c) K. Barral, J. Courcambeck, G. Pèpe, J. Balzaini, J. Neyts, E. De Clercq and M. Camplo, J. Med Chem., 2005, 48, 450 and pertinent references cited therein.
-
(2005)
J. Med. Chem.
, vol.48
, pp. 450
-
-
Barral, K.1
Courcambeck, J.2
Pèpe, G.3
Balzaini, J.4
Neyts, J.5
De Clercq, E.6
Camplo, M.7
-
10
-
-
84890743076
-
-
ed. P. A. Evans, Wiley-VCH, Weinheim, ch. 10, and pertinent references cited therein
-
For a recent review of the rhodium-catalyzed allylic substitution reaction, see: D. K. Leahy and P. A. Evans, in Modern Rhodium-Catalyzed Organic Reactions, ed. P. A. Evans, Wiley-VCH, Weinheim, 2005, ch. 10, p. 191 and pertinent references cited therein.
-
(2005)
Modern Rhodium-Catalyzed Organic Reactions
, pp. 191
-
-
Leahy, D.K.1
Evans, P.A.2
-
11
-
-
1542389323
-
-
3-benzoyl thymine, see: W. Saeyens, R. Busson, J. Van der Eycken, P. Herdewijn and D. De Keukeleire, Chem. Commun., 1997, 817.
-
(1997)
Chem. Commun.
, pp. 817
-
-
Saeyens, W.1
Busson, R.2
Van Der Eycken, J.3
Herdewijn, P.4
De Keukeleire, D.5
-
12
-
-
32844458701
-
-
note
-
The attempted allylic amination reaction with the lithium anion of thymine gave a complex mixture of products, thereby illustrating the importance of the protecting group.
-
-
-
-
13
-
-
32844456102
-
-
note
-
1 = H; 65.1 mg, 98%) as a colorless oil.
-
-
-
-
14
-
-
0033591863
-
-
(a) P. A. Evans, J. E. Robinson and J. D. Nelson, J. Am. Chem. Soc., 1999, 121, 6761;
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 6761
-
-
Evans, P.A.1
Robinson, J.E.2
Nelson, J.D.3
-
16
-
-
0035909588
-
-
(c) P. A. Evans, J. E. Robinson and K. K. Moffett, Org. Lett., 2001, 3, 3269.
-
(2001)
Org. Lett.
, vol.3
, pp. 3269
-
-
Evans, P.A.1
Robinson, J.E.2
Moffett, K.K.3
-
17
-
-
32844473550
-
-
note
-
3-benzoyl thymine.
-
-
-
-
18
-
-
0000432226
-
-
ed. I. Ojima, Wiley-VCH, New York, 2nd edn, ch. 6
-
For a review of catalytic asymmetric dihydroxylation, see: R. A. Johnson and K. B. Sharpless, in Catalytic Asymmetric Synthesis, ed. I. Ojima, Wiley-VCH, New York, 2nd edn, 2000, ch. 6, p. 357.
-
(2000)
Catalytic Asymmetric Synthesis
, pp. 357
-
-
Johnson, R.A.1
Sharpless, K.B.2
-
19
-
-
0028605353
-
-
For an example of improved enantioselectivity in the asymmetric dihydroxylation due to π-stacking, see: E. J. Corey, A. Guzman-Perez and M. C. Noe, J. Am. Chem. Soc., 1994, 116, 12109.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 12109
-
-
Corey, E.J.1
Guzman-Perez, A.2
Noe, M.C.3
-
20
-
-
0000941585
-
-
M. J. Martinelli, N. K. Nayyar, E. D. Moher, U. P. Dhokte, J. M. Pawlak and R. Vaidyanathan, Org. Lett., 1999, 1, 447.
-
(1999)
Org. Lett.
, vol.1
, pp. 447
-
-
Martinelli, M.J.1
Nayyar, N.K.2
Moher, E.D.3
Dhokte, U.P.4
Pawlak, J.M.5
Vaidyanathan, R.6
-
21
-
-
0002667764
-
-
For reviews on the Mitsunobu reaction, see: (a) O. Mitsunobu, Synthesis, 1981, 1;
-
(1981)
Synthesis
, pp. 1
-
-
Mitsunobu, O.1
-
24
-
-
0020606823
-
-
For a related example of a stereoselective free radical cyclization where a similar non-bonding interaction is invoked to rationalize the trans-diastereoselectivity, see: (a) D. J. Hart and K. Kanai, J. Am. Chem. Soc., 1983, 105, 1255;
-
(1983)
J. Am. Chem. Soc.
, vol.105
, pp. 1255
-
-
Hart, D.J.1
Kanai, K.2
-
25
-
-
0000657627
-
-
(b) A. L. J. Beckwith, S. P. Joseph and R. T. A. Mayadunne, J. Org. Chem., 1993, 58, 4198;
-
(1993)
J. Org. Chem.
, vol.58
, pp. 4198
-
-
Beckwith, A.L.J.1
Joseph, S.P.2
Mayadunne, R.T.A.3
-
26
-
-
0034623536
-
-
(c) P. A. Evans, T. Manangan and A. L. Rheingold, J. Am. Chem. Soc., 2000, 122, 11009;
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 11009
-
-
Evans, P.A.1
Manangan, T.2
Rheingold, A.L.3
-
27
-
-
28444443419
-
-
(d) P. A. Evans, T. Manangan and A. L. Rheingold, J. Am. Chem. Soc., 2005, 127, 16745.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 16745
-
-
Evans, P.A.1
Manangan, T.2
Rheingold, A.L.3
-
30
-
-
0027930134
-
-
For a related free radical reduction in a related thymine derivative, see: D. J. Fenick and D. E. Falvey, J. Org. Chem., 1994, 59, 4791.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 4791
-
-
Fenick, D.J.1
Falvey, D.E.2
-
31
-
-
32844457091
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note
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The desired product was also obtained with a minor amount of the product from the epimerization of the methyl group (≤5%).
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