-
1
-
-
0343588845
-
-
Reviews on Grignard reagents: for transition-metal-mediated reactions, see: a, Eds, G. S. Silverman, P. E. Rakita, Marcel Dekker, New York
-
Reviews on Grignard reagents: for transition-metal-mediated reactions, see: a) H. Urabe, F. Sato in Handbook of Grignard Reactions (Eds.: G. S. Silverman, P. E. Rakita), Marcel Dekker, New York, 1996, pp. 577-632.
-
(1996)
Handbook of Grignard Reactions
, pp. 577-632
-
-
Urabe, H.1
Sato, F.2
-
2
-
-
53249112786
-
-
For conjugate addition, see: b, Eds, G. S. Silverman, P. E. Rakita, Marcel Dekker, New York
-
For conjugate addition, see: b) L. Miginiac in Handbook of Grignard Reactions (Eds.: G. S. Silverman, P. E. Rakita), Marcel Dekker, New York, 1996, pp. 391-396.
-
(1996)
Handbook of Grignard Reactions
, pp. 391-396
-
-
Miginiac, L.1
-
4
-
-
0004219714
-
-
For reviews on copper-mediated conjugate addition of Grignard reagents, see: a, 2nd ed, Ed, M. Schlosser, Wiley, New York
-
For reviews on copper-mediated conjugate addition of Grignard reagents, see: a) B. H. Lipshutz in Organometallics in Organic Synthesis. A Manual, 2nd ed. (Ed.: M. Schlosser), Wiley, New York, 2002, pp. 665-815;
-
(2002)
Organometallics in Organic Synthesis. A Manual
, pp. 665-815
-
-
Lipshutz, B.H.1
-
5
-
-
0000220284
-
-
Ed, L. A. Paquette, Wiley, New York
-
b) B. H. Lipshutz, S. Sengupta in Organic Reactions, Vol. 41 (Ed.: L. A. Paquette), Wiley, New York, 1992, pp. 135-631;
-
(1992)
Organic Reactions
, vol.41
, pp. 135-631
-
-
Lipshutz, B.H.1
Sengupta, S.2
-
6
-
-
0001189279
-
-
Eds, B. M. Trost, I. Fleming, Pergamon, Oxford
-
c) B. H. Lipshutz in Comprehensive Organic Synthesis, Vol. 1 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 107-138;
-
(1991)
Comprehensive Organic Synthesis
, vol.1
, pp. 107-138
-
-
Lipshutz, B.H.1
-
7
-
-
0000696943
-
-
Eds, B. M. Trost, I. Fleming, Pergamon, Oxford
-
d) J. A. Kozlowski in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 169-198.
-
(1991)
Comprehensive Organic Synthesis
, vol.4
, pp. 169-198
-
-
Kozlowski, J.A.1
-
8
-
-
33845553723
-
-
1,4-Selective addition to α,β,γ,δ-unsaturated carbonyl compounds is little documented. For copper-catalyzed 1,4-addition to 2,4-dienoates, see: a Y. Yamamoto, S. Yamamoto, H. Yatagai, Y. Ishihara, K. Maruyama, J. Org. Chem. 1982, 47, 119-126.
-
1,4-Selective addition to α,β,γ,δ-unsaturated carbonyl compounds is little documented. For copper-catalyzed 1,4-addition to 2,4-dienoates, see: a) Y. Yamamoto, S. Yamamoto, H. Yatagai, Y. Ishihara, K. Maruyama, J. Org. Chem. 1982, 47, 119-126.
-
-
-
-
9
-
-
2342572316
-
-
For 1,4-addition of Grignard reagents to α,β,γ,δ- unsaturated amides: b F. Barbot, A. Kadib-Elban, P. Miginiac, Tetrahedron Lett. 1983, 24, 5089-5090.
-
For 1,4-addition of Grignard reagents to α,β,γ,δ- unsaturated amides: b) F. Barbot, A. Kadib-Elban, P. Miginiac, Tetrahedron Lett. 1983, 24, 5089-5090.
-
-
-
-
10
-
-
0001428047
-
-
For copper-mediated 1,6-addition to 2,4-dienoates, see: a
-
For copper-mediated 1,6-addition to 2,4-dienoates, see: a) E. J. Corey, C. U. Kim, R. H. K. Chen, M. Takeda, J. Am. Chem. Soc. 1972, 94, 4395-4396;
-
(1972)
J. Am. Chem. Soc
, vol.94
, pp. 4395-4396
-
-
Corey, E.J.1
Kim, C.U.2
Chen, R.H.K.3
Takeda, M.4
-
13
-
-
33847641409
-
-
Reference [3a]; e P. Wipf, M. Grenon, Can. J. Chem. 2006, 84, 1226-1241;
-
d) Reference [3a]; e) P. Wipf, M. Grenon, Can. J. Chem. 2006, 84, 1226-1241;
-
-
-
-
14
-
-
53249122500
-
-
f) T. den Hartog, S. R. Harutyunyan, D. Font, A. J. Minnaard, B. L. Feringa, Angew. Chem. 2008, 120, 404-407;
-
(2008)
Angew. Chem
, vol.120
, pp. 404-407
-
-
den Hartog, T.1
Harutyunyan, S.R.2
Font, D.3
Minnaard, A.J.4
Feringa, B.L.5
-
15
-
-
38049058696
-
-
Angew. Chem. Int. Ed. 2008, 47, 398-401.
-
(2008)
Angew. Chem. Int. Ed
, vol.47
, pp. 398-401
-
-
-
16
-
-
0342355883
-
-
To 2,4-dienamide, see: g) Reference [3b]. To 2,4-dienones, see: h F. Barbot, A. Kadib-Elban, P. Miginiac, J. Organomet. Chem. 1983, 255, 1-9;
-
To 2,4-dienamide, see: g) Reference [3b]. To 2,4-dienones, see: h) F. Barbot, A. Kadib-Elban, P. Miginiac, J. Organomet. Chem. 1983, 255, 1-9;
-
-
-
-
18
-
-
0242548198
-
-
j) S. P. Modi, J. O. Gardner, A. Milowsky, M. Wierzba, L. Forgione, P. Mazur, A. J. Solo, W. L. Duax, Z. Galdecki, P. Grochulski, Z. Wawrzak, J. Org. Chem. 1989, 54, 2317-2321;
-
(1989)
J. Org. Chem
, vol.54
, pp. 2317-2321
-
-
Modi, S.P.1
Gardner, J.O.2
Milowsky, A.3
Wierzba, M.4
Forgione, L.5
Mazur, P.6
Solo, A.J.7
Duax, W.L.8
Galdecki, Z.9
Grochulski, P.10
Wawrzak, Z.11
-
19
-
-
33751157701
-
-
k) H. Liu, L. M. Gayo, R. W. Sullivan, A. Y. H. Choi, H. W. Moore, J. Org. Chem. 1994, 59, 3284-3288;
-
(1994)
J. Org. Chem
, vol.59
, pp. 3284-3288
-
-
Liu, H.1
Gayo, L.M.2
Sullivan, R.W.3
Choi, A.Y.H.4
Moore, H.W.5
-
21
-
-
0001334338
-
-
To enynoates, see: m
-
To enynoates, see: m) N. Krause, A. Gerold, Angew. Chem. 1997, 109, 194-213;
-
(1997)
Angew. Chem
, vol.109
, pp. 194-213
-
-
Krause, N.1
Gerold, A.2
-
23
-
-
53249134085
-
-
Although 1,4-addition of Grignard reagents to α,β,γ, δ-unsaturated amides was reported reference [3b, the precise regioselectivities were not described and low to moderate product yields were reported. In our group, among alkyl, alkenyl, and aryl Grignard reagents, only isopropenyl-like reagents proved satisfactory for this study. For Grignard conjugate addition to α,β-unsaturated amides, see reference [1b
-
Although 1,4-addition of Grignard reagents to α,β,γ, δ-unsaturated amides was reported (reference [3b]), the precise regioselectivities were not described and low to moderate product yields were reported. In our group, among alkyl, alkenyl, and aryl Grignard reagents, only isopropenyl-like reagents proved satisfactory for this study. For Grignard conjugate addition to α,β-unsaturated amides, see reference [1b].
-
-
-
-
24
-
-
0001040147
-
-
For reviews on asymmetric conjugate additions, see: a
-
For reviews on asymmetric conjugate additions, see: a) B. E. Rossiter, N. M. Swingle, Chem. Rev. 1992, 92, 771-806;
-
(1992)
Chem. Rev
, vol.92
, pp. 771-806
-
-
Rossiter, B.E.1
Swingle, N.M.2
-
27
-
-
34249095816
-
-
d) J. Christoffers, G. Koripelly, A. Rosiak, M. Rössle, Synthesis 2007, 1279-1300;
-
(2007)
Synthesis
, pp. 1279-1300
-
-
Christoffers, J.1
Koripelly, G.2
Rosiak, A.3
Rössle, M.4
-
28
-
-
34147221694
-
-
e) F. López, A. J. Minnaard, B. L. Feringa, Acc. Chem. Res. 2007, 40, 179-188.
-
(2007)
Acc. Chem. Res
, vol.40
, pp. 179-188
-
-
López, F.1
Minnaard, A.J.2
Feringa, B.L.3
-
29
-
-
53249128468
-
-
Similar amides derived from prolinol or α,α-diphenylprolinol and amide 21 showed lower product yields and/or diastereoselectivities.
-
Similar amides derived from prolinol or α,α-diphenylprolinol and amide 21 showed lower product yields and/or diastereoselectivities.
-
-
-
-
30
-
-
0026733219
-
-
a) Y. Masaki, H. Oda, K. Kazuta, A. Usui, A. Itoh, F. Xu, Tetrahedron Lett. 1992, 33, 5089-5092;
-
(1992)
Tetrahedron Lett
, vol.33
, pp. 5089-5092
-
-
Masaki, Y.1
Oda, H.2
Kazuta, K.3
Usui, A.4
Itoh, A.5
Xu, F.6
-
32
-
-
37049096833
-
-
N. Baggett, P. Stribblehill, J. Chem. Soc. Perkin Trans. 1 1977, 1123-1126. The antipode of 3 can be prepared from commercially available L-mannitol.
-
c) N. Baggett, P. Stribblehill, J. Chem. Soc. Perkin Trans. 1 1977, 1123-1126. The antipode of 3 can be prepared from commercially available L-mannitol.
-
-
-
-
33
-
-
0001564507
-
-
For reviews on three-component coupling reactions based on conjugate addition, see: a, Ed, L. A. Paquette, Wiley, New York
-
For reviews on three-component coupling reactions based on conjugate addition, see: a) M. J. Chapdelaine, M. Hulce in Organic Reactions, Vol. 38 (Ed.: L. A. Paquette), Wiley, New York, 1990, pp. 225-653;
-
(1990)
Organic Reactions
, vol.38
, pp. 225-653
-
-
Chapdelaine, M.J.1
Hulce, M.2
-
35
-
-
30444443444
-
-
Angew. Chem. Int. Ed. 2006, 45, 354-366.
-
(2006)
Angew. Chem. Int. Ed
, vol.45
, pp. 354-366
-
-
-
36
-
-
0011844035
-
-
Precedents of three-component coupling process based on conjugate addition of organometallic reagents to acyclic chiral α,β-unsaturated carbonyl compounds followed by alkylation are as follows. In these reactions, the alkylation was achieved with reactive halides and a less reactive, higher primary-alkyl iodide, such as C6H13I, was not included; a L. S. Liebeskind, M. E. Welker, Tetrahedron Lett. 1985, 26, 3079-3082;
-
13I, was not included; a) L. S. Liebeskind, M. E. Welker, Tetrahedron Lett. 1985, 26, 3079-3082;
-
-
-
-
37
-
-
0034750713
-
-
b) K. Totani, S. Asano, K. Takao, K. Tadano, Synlett 2001, 1772-1776;
-
(2001)
Synlett
, pp. 1772-1776
-
-
Totani, K.1
Asano, S.2
Takao, K.3
Tadano, K.4
-
38
-
-
0042244168
-
-
c) Y. Arai, M. Kasai, K. Ueda, Y. Masaki, Synthesis 2003, 1511-1516;
-
(2003)
Synthesis
, pp. 1511-1516
-
-
Arai, Y.1
Kasai, M.2
Ueda, K.3
Masaki, Y.4
-
39
-
-
33749135033
-
-
d) E. Reyes, J. L. Vicario, L. Carrillo, D. Badia, U. Uria, A. Iza, J. Org. Chem. 2006, 71, 7763-7772.
-
(2006)
J. Org. Chem
, vol.71
, pp. 7763-7772
-
-
Reyes, E.1
Vicario, J.L.2
Carrillo, L.3
Badia, D.4
Uria, U.5
Iza, A.6
-
40
-
-
53249087470
-
-
For hydrolysis of amides, see:, 2nd ed, Wiley, New York, and pp
-
For hydrolysis of amides, see: T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 2nd ed., Wiley, New York, 1991, pp. 270-275 and pp. 349-357.
-
(1991)
Protective Groups in Organic Synthesis
-
-
Greene, T.W.1
Wuts, P.G.M.2
-
42
-
-
33947441665
-
-
For conjugate addition of Grignard reagents to α,β-unsaturated carbonyl compounds, few reports described an iron-catalyzed version: a M. S. Kharasch, D. C. Sayles, J. Am. Chem. Soc. 1942, 64, 2972-2975;
-
For conjugate addition of Grignard reagents to α,β-unsaturated carbonyl compounds, few reports described an iron-catalyzed version: a) M. S. Kharasch, D. C. Sayles, J. Am. Chem. Soc. 1942, 64, 2972-2975;
-
-
-
-
43
-
-
0001528112
-
-
b) S. R. Jensen, A.-M. Kristiansen, J. Munch-Petersen, Acta Chem. Scand. 1970, 24, 2641-2647;
-
(1970)
Acta Chem. Scand
, vol.24
, pp. 2641-2647
-
-
Jensen, S.R.1
Kristiansen, A.-M.2
Munch-Petersen, J.3
-
44
-
-
0000540645
-
-
c) T. Mukaiyama, T. Takeda, K. Fujimoto, Bull. Chem. Soc. Jpn. 1978, 51, 3368-3372;
-
(1978)
Bull. Chem. Soc. Jpn
, vol.51
, pp. 3368-3372
-
-
Mukaiyama, T.1
Takeda, T.2
Fujimoto, K.3
-
45
-
-
36749007137
-
-
d) Z. Lu, G. Chai, S. Ma, J. Am. Chem. Soc. 2007, 129, 14546-14547.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 14546-14547
-
-
Lu, Z.1
Chai, G.2
Ma, S.3
-
46
-
-
53249114803
-
-
Rh- or Ir-catalyzed 1,6-addition of arylboron or -zinc reagents to 2,4-dienones or -dienoates has been recently reported: a T. Hayashi, S. Yamamoto, N. Tokunaga, Angew. Chem. 2005, 117, 4296-4299;
-
Rh- or Ir-catalyzed 1,6-addition of arylboron or -zinc reagents to 2,4-dienones or -dienoates has been recently reported: a) T. Hayashi, S. Yamamoto, N. Tokunaga, Angew. Chem. 2005, 117, 4296-4299;
-
-
-
-
47
-
-
22144458723
-
-
Angew. Chem. Int. Ed. 2005, 44, 4224-4227;
-
(2005)
Angew. Chem. Int. Ed
, vol.44
, pp. 4224-4227
-
-
-
48
-
-
29444458959
-
-
b) G. de La Herrán, C. Murcia, A. G. Csákÿ, Org. Lett. 2005, 7, 5629 -5632;
-
(2005)
Org. Lett
, vol.7
, pp. 5629-5632
-
-
de La Herrán, G.1
Murcia, C.2
Csákÿ, A.G.3
-
49
-
-
53249132245
-
-
c) T. Nishimura, Y. Yasuhara, T. Hayashi, Angew. Chem. 2006, 118, 5288-5290;
-
(2006)
Angew. Chem
, vol.118
, pp. 5288-5290
-
-
Nishimura, T.1
Yasuhara, Y.2
Hayashi, T.3
-
50
-
-
33747229725
-
-
Angew. Chem. Int. Ed. 2006, 45, 5164-5166.
-
(2006)
Angew. Chem. Int. Ed
, vol.45
, pp. 5164-5166
-
-
-
51
-
-
11144323895
-
-
For reviews on iron-mediated organic reactions, see
-
For reviews on iron-mediated organic reactions, see: C. Bolm, J. Legros, J. Le Paih, L. Zani, Chem. Rev. 2004, 104, 6217-6254.
-
(2004)
Chem. Rev
, vol.104
, pp. 6217-6254
-
-
Bolm, C.1
Legros, J.2
Le Paih, J.3
Zani, L.4
-
52
-
-
0000830285
-
-
Examples of acyclic 1,n-asymmetric induction where n is more than five are rare; a H. J. Mitchell, A. Nelson, S. Warren, J. Chem. Soc. Perkin Trans. 1 1999, 1899-1914;
-
Examples of acyclic 1,n-asymmetric induction where n is more than five are rare; a) H. J. Mitchell, A. Nelson, S. Warren, J. Chem. Soc. Perkin Trans. 1 1999, 1899-1914;
-
-
-
-
53
-
-
0000458209
-
-
b) A. H. Hoveyda, D. A. Evans, G. C. Fu, Chem. Rev. 1993, 93, 1307-1370.
-
(1993)
Chem. Rev
, vol.93
, pp. 1307-1370
-
-
Hoveyda, A.H.1
Evans, D.A.2
Fu, G.C.3
-
54
-
-
53249143590
-
-
A similar amide derived from α,α-diphenylprolinol and amide 3 showed lower diastereoselectvities.
-
A similar amide derived from α,α-diphenylprolinol and amide 3 showed lower diastereoselectvities.
-
-
-
-
55
-
-
0034733548
-
-
a) D. J. Aldous, W. M. Dutton, P. G. Steel, Tetrahedron: Asymmetry 2000, 11, 2455-2462;
-
(2000)
Tetrahedron: Asymmetry
, vol.11
, pp. 2455-2462
-
-
Aldous, D.J.1
Dutton, W.M.2
Steel, P.G.3
-
56
-
-
0000483985
-
-
W. F. Jarvis, M. D. Hoey, A. L. Finocchio, D. C. Dittmer, J. Org. Chem. 1988, 53, 5750-5756. The antipode of 21 is also available by this method.
-
b) W. F. Jarvis, M. D. Hoey, A. L. Finocchio, D. C. Dittmer, J. Org. Chem. 1988, 53, 5750-5756. The antipode of 21 is also available by this method.
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-
-
-
57
-
-
53249155542
-
-
For s-cis-diene-iron complexes, see: a Comprehensive Organometallic Chemistry, 4 (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Pergamon, Oxford, 1982, pp. 243-649;
-
For s-cis-diene-iron complexes, see: a) Comprehensive Organometallic Chemistry, Vol. 4 (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Pergamon, Oxford, 1982, pp. 243-649;
-
-
-
-
58
-
-
0004219714
-
-
2nd ed, Ed, M. Schlosser, Wiley, New York
-
b) M. F. Semmelhack in Organometallics in Organic Synthesis. A Manual, 2nd ed. (Ed.: M. Schlosser), Wiley, New York, 2002, pp. 1006-1121;
-
(2002)
Organometallics in Organic Synthesis. A Manual
, pp. 1006-1121
-
-
Semmelhack, M.F.1
-
59
-
-
0037847963
-
-
c) D. C. Knölker, Chem. Rev. 2000, 100, 2941-2961.
-
(2000)
Chem. Rev
, vol.100
, pp. 2941-2961
-
-
Knölker, D.C.1
-
60
-
-
53249139265
-
-
Although we used a sample of 97%ee for this study, the parent amine of 99%ee is also available. See reference [18
-
Although we used a sample of 97%ee for this study, the parent amine of 99%ee is also available. See reference [18].
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