-
1
-
-
0000677232
-
-
(a) Li, C.-J. Chem. Rev. 1993, 93, 2023.
-
(1993)
Chem. Rev.
, vol.93
, pp. 2023
-
-
Li, C.-J.1
-
3
-
-
0003768632
-
-
Anastas, P., Williamson, T., Eds.; Oxford University Press: New York
-
(c) Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P., Williamson, T., Eds.; Oxford University Press: New York, 1998.
-
(1998)
Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing
-
-
Paquette, L.A.1
-
6
-
-
33751386227
-
-
(b) Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500.
-
(1993)
J. Org. Chem.
, vol.58
, pp. 5500
-
-
Kim, E.1
Gordon, D.M.2
Schmid, W.3
Whitesides, G.M.4
-
9
-
-
0028006273
-
-
(a) Binder, W. H.; Prenner, R. H.; Schmid, W. Tetrahedron 1994, 50, 749.
-
(1994)
Tetrahedron
, vol.50
, pp. 749
-
-
Binder, W.H.1
Prenner, R.H.2
Schmid, W.3
-
14
-
-
0032572905
-
-
and references cited therein
-
(c) Araki, S.; Nakano, H.; Subburaj, K.; Hirashita, T.; Shibutani, K.; Yamamura, H.; Kawai, M.; Butsugan, Y. Tetrahedron Lett. 1998, 39, 6327 and references cited therein.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 6327
-
-
Araki, S.1
Nakano, H.2
Subburaj, K.3
Hirashita, T.4
Shibutani, K.5
Yamamura, H.6
Kawai, M.7
Butsugan, Y.8
-
15
-
-
84989456545
-
-
For reviews, see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841. (b) Oppolzer, W. Angew, Chem., Int. Ed. Engl. 1989, 28, 38. (c) Knochel, P. Carbometalation of Alkenes and Alkynes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 865-911.
-
(1981)
Synthesis
, pp. 841
-
-
Normant, J.F.1
Alexakis, A.2
-
16
-
-
84990107570
-
-
For reviews, see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841. (b) Oppolzer, W. Angew, Chem., Int. Ed. Engl. 1989, 28, 38. (c) Knochel, P. Carbometalation of Alkenes and Alkynes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 865-911.
-
(1989)
Angew, Chem., Int. Ed. Engl.
, vol.28
, pp. 38
-
-
Oppolzer, W.1
-
17
-
-
0001522634
-
Carbometalation of Alkenes and Alkynes
-
Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York
-
For reviews, see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841. (b) Oppolzer, W. Angew, Chem., Int. Ed. Engl. 1989, 28, 38. (c) Knochel, P. Carbometalation of Alkenes and Alkynes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 865-911.
-
(1991)
Comprehensive Organic Synthesis
, vol.4
, pp. 865-911
-
-
Knochel, P.1
-
18
-
-
0026530298
-
-
Araki, S.; Imai, A.; Shimizu, K.; Butsugan, Y. Tetrahedron Lett. 1992, 33, 2581.
-
(1992)
Tetrahedron Lett.
, vol.33
, pp. 2581
-
-
Araki, S.1
Imai, A.2
Shimizu, K.3
Butsugan, Y.4
-
20
-
-
0000656554
-
-
Araki, S.; Imai, A.; Shimizu, K.; Yamada, M.; Mori, A.; Butsugan, Y. J. Org. Chem. 1995, 60, 1841.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 1841
-
-
Araki, S.1
Imai, A.2
Shimizu, K.3
Yamada, M.4
Mori, A.5
Butsugan, Y.6
-
22
-
-
0033612233
-
-
After this paper was submitted, an addional report was published: (b) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4095.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 4095
-
-
Fujiwara, N.1
Yamamoto, Y.2
-
23
-
-
33845278851
-
-
Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831.
-
(1988)
Org. Chem.
, vol.53
, pp. 1831
-
-
Araki, S.1
Ito, H.2
Butsugan, Y.J.3
-
24
-
-
0344338341
-
-
note
-
We interpret the beneficial yields to arise from a loss of chelation upon the addition of TMSCl, which destabilizes the vinylic indium intermediate and thereby facilitates the subsequent aqueous workup. No In-Si interchange was observed.
-
-
-
-
26
-
-
0345632804
-
-
note
-
1H NMR spectroscopy).
-
-
-
-
27
-
-
0344338338
-
-
note
-
The observation of probable radical pathways in carboindation reactions has been described; see ref 9.
-
-
-
-
28
-
-
0344770339
-
-
note
-
The double substitution of carboindation products might proceed by a fast consecutive exchange, possibly via intermediacy of a sterically less crowded haloindium carbenoid.
-
-
-
-
29
-
-
1642397559
-
-
See, for example, in carbocuprations: Alexakis, A.; Commerçon, A.; Coulentianos, C.; Normant, J. F. Tetrahedron 1984, 40, 715.
-
(1984)
Tetrahedron
, vol.40
, pp. 715
-
-
Alexakis, A.1
Commerçon, A.2
Coulentianos, C.3
Normant, J.F.4
-
30
-
-
0344338337
-
-
note
-
Linear 1,4-dienes were found to have the E configuration, as a result of syn addition of the organoindium reagent. No Z-dienes were detected; see ref 9.
-
-
-
-
31
-
-
0345632800
-
-
note
-
The origin of the differences for 17a and 17b might arise from enhanced steric crowding in the bicyclic chelated transition state for 17b relative to that for 17a. Alternatively, chelation in the bicyclic transition state for 17b might be destabilized relative to that for 17a due to the presence of the electron-withdrawing ester group in 17b.
-
-
-
-
32
-
-
0001015055
-
-
Therefore, the carboxylic acid moiety is not as strongly chelating as the hydroxyl moiety in this case, which contrasts the findings in carbonyl addition reactions; see: Bernardelli, P.; Paquette, L. A. J. Org. Chem. 1997, 62, 8284.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 8284
-
-
Bernardelli, P.1
Paquette, L.A.2
-
33
-
-
0344338336
-
-
note
-
In carbonyl addition reactions only two of three ligands typically react; see ref 11.
-
-
-
-
34
-
-
0001120461
-
-
Paquette, L. A.; Rothhaar, R. R.; Isaac, M.; Rogers, L.; Rogers, R. D. J. Org. Chem. 1998, 63, 5463.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 5463
-
-
Paquette, L.A.1
Rothhaar, R.R.2
Isaac, M.3
Rogers, L.4
Rogers, R.D.5
-
35
-
-
0344338335
-
-
note
-
A possible fast intramolecular proton transfer (via a six-membered ring) from the hydroxy group to the In-centered carbon would result in "quenching" of the In atom in syn orientation to the hydroxy group.
-
-
-
-
38
-
-
33947087906
-
-
1a: Kwart, H.; Sarner, S. F.; Slutsky, J. J. Am. Chem. Soc. 1973, 95, 5234. 1c: Logue, M. W.; Teng, K. J. Org. Chem. 1982, 47, 2549.
-
(1973)
J. Am. Chem. Soc.
, vol.95
, pp. 5234
-
-
Kwart, H.1
Sarner, S.F.2
Slutsky, J.3
-
39
-
-
0001103972
-
-
1a: Kwart, H.; Sarner, S. F.; Slutsky, J. J. Am. Chem. Soc. 1973, 95, 5234. 1c: Logue, M. W.; Teng, K. J. Org. Chem. 1982, 47, 2549.
-
(1982)
J. Org. Chem.
, vol.47
, pp. 2549
-
-
Logue, M.W.1
Teng, K.2
-
41
-
-
0345632798
-
-
Miyamo, S.; Mori, A.; Kato, K.; Kawashima, Y.; Hashimoto, H. Chem. Lett. 1982, 1379. For the corresponding linear diene, see: Ramana, C. V.; Reddy, K. R.; Nagarajan, M. Indian J. Chem. Sect. B 1996, 534.
-
(1982)
Chem. Lett.
, vol.1379
-
-
Miyamo, S.1
Mori, A.2
Kato, K.3
Kawashima, Y.4
Hashimoto, H.5
-
42
-
-
2842524853
-
-
Miyamo, S.; Mori, A.; Kato, K.; Kawashima, Y.; Hashimoto, H. Chem. Lett. 1982, 1379. For the corresponding linear diene, see: Ramana, C. V.; Reddy, K. R.; Nagarajan, M. Indian J. Chem. Sect. B 1996, 534.
-
(1996)
Indian J. Chem. Sect. B
, pp. 534
-
-
Ramana, C.V.1
Reddy, K.R.2
Nagarajan, M.3
-
43
-
-
0027481622
-
-
Llebaria, A.; Camps, F.; Moreto, J. M. Tetrahedron 1993, 49, 1283.
-
(1993)
Tetrahedron
, vol.49
, pp. 1283
-
-
Llebaria, A.1
Camps, F.2
Moreto, J.M.3
-
45
-
-
37049085907
-
-
Crombie, L.; Rainbow, L. J. J. Chem. Soc., Perkin Trans. 1 1994, 6, 673.
-
(1994)
J. Chem. Soc., Perkin Trans. 1
, vol.6
, pp. 673
-
-
Crombie, L.1
Rainbow, L.J.2
-
47
-
-
0342658483
-
-
Lai, M.-T.; Li, D.; Oh, E.; Liu, H.-M. J. Am. Chem. Soc. 1993, 115, 1619.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 1619
-
-
Lai, M.-T.1
Li, D.2
Oh, E.3
Liu, H.-M.4
-
49
-
-
0345200958
-
-
Itoh, K.; Nishiyama, H. Heterocycles 1984, 21, 449. For the corresponding E-isomer, see: Ishino, Y.; Wakamoto, K.; Hirashima, T. Chem. Lett. 1984, 765.
-
(1984)
Heterocycles
, vol.21
, pp. 449
-
-
Itoh, K.1
Nishiyama, H.2
-
50
-
-
0345632796
-
-
Itoh, K.; Nishiyama, H. Heterocycles 1984, 21, 449. For the corresponding E-isomer, see: Ishino, Y.; Wakamoto, K.; Hirashima, T. Chem. Lett. 1984, 765.
-
(1984)
Chem. Lett.
, pp. 765
-
-
Ishino, Y.1
Wakamoto, K.2
Hirashima, T.3
|