-
2
-
-
17044405496
-
-
(b) Wang, Y.; Tennyson, R. L.; Romo, D. Heterocycles 2004, 64, 605.
-
(2004)
Heterocycles
, vol.64
, pp. 605
-
-
Wang, Y.1
Tennyson, R.L.2
Romo, D.3
-
3
-
-
2342504471
-
-
For more recent advances, see: c
-
For more recent advances, see: (c) Zhu, C.; Shen, X.; Nelson, S. G. J. Am. Chem. Soc. 2004, 126, 5352.
-
(2004)
J. Am. Chem. Soc
, vol.126
, pp. 5352
-
-
Zhu, C.1
Shen, X.2
Nelson, S.G.3
-
4
-
-
11144311055
-
-
Wilson, J. E.; Fu, G. Agnew. Chem., Int. Ed. 2004, 43, 6358.
-
(d) Wilson, J. E.; Fu, G. Agnew. Chem., Int. Ed. 2004, 43, 6358.
-
-
-
-
5
-
-
18844407281
-
-
(e) Calter, M. A.; Tretyak, O. A.; Flaschenriem, C. Org. Lett. 2005, 7, 1809.
-
(2005)
Org. Lett
, vol.7
, pp. 1809
-
-
Calter, M.A.1
Tretyak, O.A.2
Flaschenriem, C.3
-
6
-
-
17044369204
-
-
(f) Oh, S. H.; Cortez, G. S.; Romo, D. J. Org. Chem. 2005, 70, 2835.
-
(2005)
J. Org. Chem
, vol.70
, pp. 2835
-
-
Oh, S.H.1
Cortez, G.S.2
Romo, D.3
-
8
-
-
33748590526
-
-
(h) Kramer, J. W.; Lobkovsky, E. B.; Coates, G. W. Org. Lett. 2006, 8, 3709.
-
(2006)
Org. Lett
, vol.8
, pp. 3709
-
-
Kramer, J.W.1
Lobkovsky, E.B.2
Coates, G.W.3
-
11
-
-
4043159247
-
-
For selected recent examples, see: c
-
For selected recent examples, see: (c) Donohoe, T. J.; Sintim, H. O.; Sisangia, L.; Harling, J. D. Angew. Chem., Int. Ed. 2004, 43, 2293.
-
(2004)
Angew. Chem., Int. Ed
, vol.43
, pp. 2293
-
-
Donohoe, T.J.1
Sintim, H.O.2
Sisangia, L.3
Harling, J.D.4
-
12
-
-
3042813865
-
-
(d) Getzle, Y. D. Y. L.; Kundnani, V.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2004, 126, 6842.
-
(2004)
J. Am. Chem. Soc
, vol.126
, pp. 6842
-
-
Getzle, Y.D.Y.L.1
Kundnani, V.2
Lobkovsky, E.B.3
Coates, G.W.4
-
13
-
-
18844407281
-
-
(e) Calter, M. A.; Tretyak, O. A.; Flaschenriem, C. Org. Lett. 2005, 7, 1809.
-
(2005)
Org. Lett
, vol.7
, pp. 1809
-
-
Calter, M.A.1
Tretyak, O.A.2
Flaschenriem, C.3
-
15
-
-
33745018360
-
-
(g) Shen, X.; Wasmuth, A. S.; Zhao, J.; Zhu, C.; Nelson, S. G. J. Am. Chem. Soc. 2006, 128, 7438.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 7438
-
-
Shen, X.1
Wasmuth, A.S.2
Zhao, J.3
Zhu, C.4
Nelson, S.G.5
-
16
-
-
33749027460
-
-
(h) Henry-Riyad, H.; Lee, C.; Purohit, V. C.; Romo, D. Org. Lett. 2006, 8, 4363.
-
(2006)
Org. Lett
, vol.8
, pp. 4363
-
-
Henry-Riyad, H.1
Lee, C.2
Purohit, V.C.3
Romo, D.4
-
18
-
-
0034808095
-
-
(a) Cortez, G. S.; Tennyson, R. L.; Romo, D. J. Am. Chem. Soc. 2001, 123, 7945.
-
(2001)
J. Am. Chem. Soc
, vol.123
, pp. 7945
-
-
Cortez, G.S.1
Tennyson, R.L.2
Romo, D.3
-
20
-
-
34250685564
-
-
See also ref 1f
-
(c) See also ref 1f.
-
-
-
-
21
-
-
33749027460
-
-
Riyad, H.; Lee, C. S.; Purohit, V.; Romo, D. Org. Lett. 2006, 8, 4363.
-
(2006)
Org. Lett
, vol.8
, pp. 4363
-
-
Riyad, H.1
Lee, C.S.2
Purohit, V.3
Romo, D.4
-
22
-
-
0037178969
-
-
For additions of heteroatom nucleophiles to bicyclic β-lactones, see: a, 7075. For other examples of additions to monocyclic-β-lactones, see
-
For additions of heteroatom nucleophiles to bicyclic β-lactones, see: (a) Yokota, Y.; Cortez, G. S.; Romo, D. Tetrahedron 2002, 58, 7075. For other examples of additions to monocyclic-β-lactones, see:
-
(2002)
Tetrahedron
, vol.58
-
-
Yokota, Y.1
Cortez, G.S.2
Romo, D.3
-
23
-
-
34250677885
-
-
ref 2
-
(b) ref 2.
-
-
-
-
24
-
-
0037178970
-
-
(c) Nelson, S. G.; Spencer, K. L; Cheung, W. S.; Mamie, S. J. Tetrahedron 2002, 58, 7081.
-
(2002)
Tetrahedron
, vol.58
, pp. 7081
-
-
Nelson, S.G.1
Spencer, K.L.2
Cheung, W.S.3
Mamie, S.J.4
-
25
-
-
0000059963
-
-
(a) Normant, J. F.; Alexakis, A.; Cahiez, G. Tetrahedron Lett. 1980, 21, 935.
-
(1980)
Tetrahedron Lett
, vol.21
, pp. 935
-
-
Normant, J.F.1
Alexakis, A.2
Cahiez, G.3
-
26
-
-
0002682386
-
-
(b) Sato, T.; Kawara, T.; Kawashima, M.; Fujisawa, T. Chem. Lett. 1980, 571.
-
(1980)
Chem. Lett
, pp. 571
-
-
Sato, T.1
Kawara, T.2
Kawashima, M.3
Fujisawa, T.4
-
27
-
-
0001280607
-
-
(c) Sato, T.; Kawara, T.; Nishizawa, A.; Fujisawa, T. Tetrahedron Lett. 1980, 21, 3377.
-
(1980)
Tetrahedron Lett
, vol.21
, pp. 3377
-
-
Sato, T.1
Kawara, T.2
Nishizawa, A.3
Fujisawa, T.4
-
28
-
-
0000869758
-
-
(d) Fujisawa, T.; Sato, T.; Kawara, T.; Ohashi, K. Tetrahedron Lett. 1981, 22, 4823.
-
(1981)
Tetrahedron Lett
, vol.22
, pp. 4823
-
-
Fujisawa, T.1
Sato, T.2
Kawara, T.3
Ohashi, K.4
-
29
-
-
0009087114
-
-
(e) Sato, T.; Naruse, K.; Fujisawa, T. Tetrahedron Lett. 1982, 23, 3587.
-
(1982)
Tetrahedron Lett
, vol.23
, pp. 3587
-
-
Sato, T.1
Naruse, K.2
Fujisawa, T.3
-
30
-
-
0003051980
-
-
(f) Sato, T.; Itoh, T.; Hatori, C.; Fujisawa, T. Chem. Lett. 1983, 1391.
-
(1983)
Chem. Lett
, pp. 1391
-
-
Sato, T.1
Itoh, T.2
Hatori, C.3
Fujisawa, T.4
-
31
-
-
0022354620
-
-
(g) Arnold, L. D.; Kalantar, T. H.; Vederas, J. C. J. Am. Chem. Soc. 1985, 107, 7105.
-
(1985)
J. Am. Chem. Soc
, vol.107
, pp. 7105
-
-
Arnold, L.D.1
Kalantar, T.H.2
Vederas, J.C.3
-
32
-
-
0000242199
-
-
(h) Arnold, L. D.; Kalantar, T. H.; Vederas, J. C. J. Am. Chem. Soc. 1987, 109, 4649.
-
(1987)
J. Am. Chem. Soc
, vol.109
, pp. 4649
-
-
Arnold, L.D.1
Kalantar, T.H.2
Vederas, J.C.3
-
33
-
-
0000485135
-
-
(i) Kawashima, M.; Sato, T.; Fujisawa, T. Tetrahedron 1989, 45, 403.
-
(1989)
Tetrahedron
, vol.45
, pp. 403
-
-
Kawashima, M.1
Sato, T.2
Fujisawa, T.3
-
34
-
-
0037067526
-
-
(a) Nelson, S. G.; Wan, Z.; Stan, M. A. J. Org. Chem. 2002, 67, 4680.
-
(2002)
J. Org. Chem
, vol.67
, pp. 4680
-
-
Nelson, S.G.1
Wan, Z.2
Stan, M.A.3
-
35
-
-
13544274451
-
-
(b) Smith, N. D.; Wohlrab, A. M.; Goodman, M. Org. Lett. 2005, 7, 255.
-
(2005)
Org. Lett
, vol.7
, pp. 255
-
-
Smith, N.D.1
Wohlrab, A.M.2
Goodman, M.3
-
36
-
-
34250684378
-
-
The report from the Goodman group (ref 7b) made extensive use of chloro Grignard-derived cuprates but no rationalization was provided.
-
The report from the Goodman group (ref 7b) made extensive use of chloro Grignard-derived cuprates but no rationalization was provided.
-
-
-
-
37
-
-
0029609846
-
-
For recent reports of invertive cleavage of β-lactones with various nucleophiles, see: a
-
For recent reports of invertive cleavage of β-lactones with various nucleophiles, see: (a) Castagnani, R.; De Angelis, F.; De Fusco, E.; Giannessi, F.; Misiti, D.; Meloni, D.; Tinti, M. O. J. Org. Chem. 1995, 60, 8318.
-
(1995)
J. Org. Chem
, vol.60
, pp. 8318
-
-
Castagnani, R.1
De Angelis, F.2
De Fusco, E.3
Giannessi, F.4
Misiti, D.5
Meloni, D.6
Tinti, M.O.7
-
38
-
-
0000495414
-
-
(b) Bernabei, I.; Castagnani, R.; De angelis, F.; De Fusco, E.; Giannessi, F.; Misiti, D.; Muck, S.; Scafetta, N.; Tinti, M. O. Chem. Eur. J. 1996, 2, 826.
-
(1996)
Chem. Eur. J
, vol.2
, pp. 826
-
-
Bernabei, I.1
Castagnani, R.2
De angelis, F.3
De Fusco, E.4
Giannessi, F.5
Misiti, D.6
Muck, S.7
Scafetta, N.8
Tinti, M.O.9
-
39
-
-
0034599875
-
-
(c) Nelson, S. G.; Spencer, K. L. Angew. Chem., Int. Ed. 2000, 39, 1323.
-
(2000)
Angew. Chem., Int. Ed
, vol.39
, pp. 1323
-
-
Nelson, S.G.1
Spencer, K.L.2
-
40
-
-
34250672197
-
-
Reference 5
-
(d) Reference 5.
-
-
-
-
41
-
-
34250671345
-
-
Nelson previously employed similar conditions for additions to monocyclic-β-lactones, see ref 7a
-
Nelson previously employed similar conditions for additions to monocyclic-β-lactones, see ref 7a.
-
-
-
-
42
-
-
34250641711
-
-
In this instance, the dioxolane was prone to hydrolysis during reaction workup
-
In this instance, the dioxolane was prone to hydrolysis during reaction workup.
-
-
-
-
43
-
-
33947434903
-
-
For the earliest report of magnesium halide opening of β-lactones, see
-
For the earliest report of magnesium halide opening of β-lactones, see: Gresham, T. L.; Jansen, J. E.; Shaver, F. W.; Bankert, R. A. J. Am. Chem. Soc. 1949, 71, 2807.
-
(1949)
J. Am. Chem. Soc
, vol.71
, pp. 2807
-
-
Gresham, T.L.1
Jansen, J.E.2
Shaver, F.W.3
Bankert, R.A.4
-
44
-
-
33947267238
-
-
Gilman, H.; Jones, R. G.; Woods, L. A. J. Org. Chem. 1952, 17, 1630.
-
(1952)
J. Org. Chem
, vol.17
, pp. 1630
-
-
Gilman, H.1
Jones, R.G.2
Woods, L.A.3
-
46
-
-
0037047534
-
-
Palucki, M.; Um, J. M.; Yasuda, N.; Conlon, D. A.; Tsay, F. R.; Hartner, F. W.; Hsiao, Y.; Marcune, B.; Karady, S.; Hughes, D. L.; Dormer, P. G.; Reider, P. J. J. Org. Chem. 2002, 67, 5508.
-
(2002)
J. Org. Chem
, vol.67
, pp. 5508
-
-
Palucki, M.1
Um, J.M.2
Yasuda, N.3
Conlon, D.A.4
Tsay, F.R.5
Hartner, F.W.6
Hsiao, Y.7
Marcune, B.8
Karady, S.9
Hughes, D.L.10
Dormer, P.G.11
Reider, P.J.12
-
47
-
-
21844444522
-
-
Conlon, D. A.; Jensen, M. S.; Plaucki, M.; Yasuda, N.; Um, J. M.; Yang, C.; Hartner, F. W.; Tsay, F.-R.; Hsiao, Y.; Pye, P.; Rivera, N. R.; Hughes, D. L. Chirality 2005, 17, S149.
-
(2005)
Chirality
, vol.17
-
-
Conlon, D.A.1
Jensen, M.S.2
Plaucki, M.3
Yasuda, N.4
Um, J.M.5
Yang, C.6
Hartner, F.W.7
Tsay, F.-R.8
Hsiao, Y.9
Pye, P.10
Rivera, N.R.11
Hughes, D.L.12
-
48
-
-
85077990318
-
-
For a review describing Grignard reagents that are difficult to generate with chemically activated magnesium, see: Lai, Y. Synthesis 1981, 585
-
For a review describing Grignard reagents that are difficult to generate with chemically activated magnesium, see: Lai, Y. Synthesis 1981, 585.
-
-
-
-
49
-
-
34250690640
-
-
Employing <0.1 equiv of 1,2-dibromoethane to further minimize MgXBr concentration led to lower conversion to the Grignard reagent.
-
Employing <0.1 equiv of 1,2-dibromoethane to further minimize MgXBr concentration led to lower conversion to the Grignard reagent.
-
-
-
-
50
-
-
0000833130
-
-
Bertz, S. H.; Gibson, C. P.; Dabbagh, G. Tetrahedron Lett. 1987, 28, 4251.
-
(1987)
Tetrahedron Lett
, vol.28
, pp. 4251
-
-
Bertz, S.H.1
Gibson, C.P.2
Dabbagh, G.3
-
51
-
-
0037073198
-
-
For some recent examples, see: a
-
For some recent examples, see: (a) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 13362.
-
(2002)
J. Am. Chem. Soc
, vol.124
, pp. 13362
-
-
Degrado, S.J.1
Mizutani, H.2
Hoveyda, A.H.3
-
52
-
-
23944499068
-
-
(b) King, H. D.; Meng, Z.; Denhart, D.; Mattson, R.; Kumura, R.; Wu, D.; Gao, Q.; Macor, J. E. Org. Lett. 2005, 7, 3437.
-
(2005)
Org. Lett
, vol.7
, pp. 3437
-
-
King, H.D.1
Meng, Z.2
Denhart, D.3
Mattson, R.4
Kumura, R.5
Wu, D.6
Gao, Q.7
Macor, J.E.8
|