-
1
-
-
20544450502
-
-
2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim
-
(1)(a) Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004.
-
(2004)
Metal-Catalyzed Cross-Coupling Reactions
-
-
-
3
-
-
0003544583
-
-
2nd ed.; Ojima, I, Ed.; Wiley-VCH: New York
-
(2)(a) Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I, Ed.; Wiley-VCH: New York, 2000.
-
(2000)
Catalytic Asymmetric Synthesis
-
-
-
4
-
-
4043123499
-
-
(b) Tietze, L. F.; Ila, H.; Bell, H. P. Chem. Rev. 2004, 104, 3453-3516.
-
(2004)
Chem. Rev.
, vol.104
, pp. 3453-3516
-
-
Tietze, L.F.1
Ila, H.2
Bell, H.P.3
-
6
-
-
77949342065
-
-
Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer Verlag: Heidelberg, Chapt. 25.
-
(d) Hayashi, T. Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer Verlag: Heidelberg, 1999; Vol.II, Chapt. 25.
-
(1999)
Comprehensive Asymmetric Catalysis
, vol.2
-
-
Hayashi, T.1
-
8
-
-
77949376555
-
-
The trivial case of cross-coupling of chiral subunits where the newly formed carbon-carbon bond is not a stereogenic unit is excluded.
-
The trivial case of cross-coupling of chiral subunits where the newly formed carbon-carbon bond is not a stereogenic unit is excluded.
-
-
-
-
9
-
-
38049017956
-
-
By far the largest category of transition-metal-catalyzed, carboncarbon and carbon-heteroatom bond-forming reactions involves the asymmetric capture of π-allylmetals derived from palladium, molybdenum, rhodium, and iridium with a wide range of nucleophiles. These powerful reactions have been thoroughly reviewed and therefore will not be categorized here. See: (a) Lu, Z.; Ma, S. Angew. Chem., Int. Ed. 2008, 47, 258-297.
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 258-297
-
-
Lu, Z.1
Ma, S.2
-
11
-
-
0000345527
-
-
Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer Verlag: Heidelberg, Chapt. 24.
-
(c) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer Verlag: Heidelberg, 1999; Vol.II, Chapt. 24.
-
(1999)
Comprehensive Asymmetric Catalysis
, vol.2
-
-
Pfaltz, A.1
In, L.M.2
-
12
-
-
0000554723
-
ALlylation of Carbonyls: Methodology and stereochemistry
-
Otera, J., Ed.; Wiley-VCH: Weinheim
-
For a definition of internal and external selection, see: Denmark, S. E.; Almstead, N. G. Allylation of Carbonyls: Methodology and Stereochemistry. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; pp 299-402.
-
(2000)
Modern Carbonyl Chemistry
, pp. 299-402
-
-
Denmark, S.E.1
Almstead, N.G.2
-
13
-
-
0028355054
-
-
(6)(a) Hatanaka, Y.; Goda, K.-I.; Hiyama, T. Tetrahedron Lett. 1994, 35, 1279-1282.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 1279-1282
-
-
Hatanaka, Y.1
Goda, K.-I.2
Hiyama, T.3
-
14
-
-
0000511533
-
-
(b) Hiyama, T.; Matsuhashi, H.; Fujita, A.; Tanaka, M.; Hirabayashi, K.; Shimizu, M.; Mori, A. Organometallics 1996, 15, 5762-5765.
-
(1996)
Organometallics
, vol.15
, pp. 5762-5765
-
-
Hiyama, T.1
Matsuhashi, H.2
Fujita, A.3
Tanaka, M.4
Hirabayashi, K.5
Shimizu, M.6
Mori, A.7
-
16
-
-
35548964277
-
-
Hayashi, S.; Hirano, K.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2007, 129, 12650-12651.
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 12650-12651
-
-
Hayashi, S.1
Hirano, K.2
Yorimitsu, H.3
Oshima, K.4
-
17
-
-
38049062493
-
-
Recently developed, transition-metal-catalyzed additions of organic groups to aldehydes and imines are also not considered to be crosscoupling reactions. See: (a) Skukas, E.; Ngai, M.-Y.; Komanduri, V.; Krische, M. J. Acc Chem. Res. 2007, 40, 1394-1401.
-
(2007)
Acc Chem. Res.
, vol.40
, pp. 1394-1401
-
-
Skukas, E.1
Ngai, M.-Y.2
Komanduri, V.3
Krische, M.J.4
-
18
-
-
64849085420
-
-
(b) Patman, R. L.; Bower, J. F.; Kim, I. S.; Krische, M. J. Aldrichim. Acta 2008, 41, 95-104.
-
(2008)
Aldrichim. Acta
, vol.41
, pp. 95-104
-
-
Patman, R.L.1
Bower, J.F.2
Kim, I.S.3
Krische, M.J.4
-
19
-
-
24644462889
-
-
(9)(a) Bringmann, G.; Mortimer, A. J. P.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. Angew. Chem., Int. Ed. 2005, 44, 5384-5427.
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 5384-5427
-
-
Bringmann, G.1
Mortimer, A.J.P.2
Keller, P.A.3
Gresser, M.J.4
Garner, J.5
Breuning, M.6
-
20
-
-
0025164652
-
-
(b) Bringmann, G.; Walter, R.; Wirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977-991.
-
(1990)
Angew. Chem., Int. Ed. Engl.
, vol.29
, pp. 977-991
-
-
Bringmann, G.1
Walter, R.2
Wirich, R.3
-
22
-
-
70349782336
-
-
(b) Rudolph, A.; Lautens, M. Angew. Chem., Int. Ed. 2009, 48, 2656-2670.
-
(2009)
Angew. Chem., Int. Ed.
, vol.48
, pp. 2656-2670
-
-
Rudolph, A.1
Lautens, M.2
-
23
-
-
12344334436
-
-
(11)(a) Shibasaki, M.; Vogl, E. M.; Ohshima, T. Adv. Synth. Catal. 2004, 346, 1533-1552.
-
(2004)
Adv. Synth. Catal.
, vol.346
, pp. 1533-1552
-
-
Shibasaki, M.1
Vogl, E.M.2
Ohshima, T.3
-
24
-
-
77949413758
-
-
de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Chapt. 5.
-
(b) Bräse, S.; de Meijere, A. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; Vol.2, Chapt. 5.
-
(2004)
Metal-Catalyzed Cross-Coupling Reactions
, vol.2
-
-
Bräse, S.1
De In, M.A.2
-
26
-
-
33749324191
-
-
(12)(a) Yamamoto, Y.; Takada, S.; Miyaura, N. Chem. Lett. 2006, 35, 704-705.
-
(2006)
Chem. Lett.
, vol.35
, pp. 704-705
-
-
Yamamoto, Y.1
Takada, S.2
Miyaura, N.3
-
27
-
-
33847668460
-
-
(b) Yamamoto, Y.; Takada, S.; Miyaura, N. Chem. Lett. 2006, 35, 1368-1369.
-
(2006)
Chem. Lett.
, vol.35
, pp. 1368-1369
-
-
Yamamoto, Y.1
Takada, S.2
Miyaura, N.3
-
28
-
-
61849093079
-
-
(c) Yamamoto, Y.; Takada, S.; Miyaura, N.; Iyama, T.; Tachikawa, H. Organometallics 2009, 28, 152-160.
-
(2009)
Organometallics
, vol.28
, pp. 152-160
-
-
Yamamoto, Y.1
Takada, S.2
Miyaura, N.3
Iyama, T.4
Tachikawa, H.5
-
31
-
-
70350506377
-
-
(14)(a) Kozlowski, M. C.; Morgan, B. J.; Linton, E. C. Chem. Soc. Rev. 2009, 38, 3193-3207.
-
(2009)
Chem. Soc. Rev.
, vol.38
, pp. 3193-3207
-
-
Kozlowski, M.C.1
Morgan, B.J.2
Linton, E.C.3
-
33
-
-
0035903503
-
-
(c) Bolm, C.; Hildebrand, J. P.; Muñiz, K.; Hermanns, N. Angew. Chem., Int. Ed 2001, 40, 3284-3308.
-
(2001)
Angew. Chem., Int. Ed
, vol.40
, pp. 3284-3308
-
-
Bolm, C.1
Hildebrand, J.P.2
Muñiz, K.3
Hermanns, N.4
-
36
-
-
49049101971
-
-
Chiral, olefinic ligands are widely employed in asymmetric, transitionmetal-catalyzed reactions. However, their use in asymmetric, palladium-catalyzed reactions remains elusive. See: Defieber, C.; Grützmacher, H.; Carreira, E. M. Angew. Chem., Int. Ed. 2008, 47, 4482-4502.
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 4482-4502
-
-
Defieber, C.1
Grützmacher, H.2
Carreira, E.M.3
-
37
-
-
21344470856
-
-
Trauner reported the preparation of a chiral diene-ligated palladium catalyst; however, the use of this catalyst in a palladium ene reaction provided only racemic products. See: Grundl, M. A.; Kennedy-Smith, J. J.; Trauner, D. Organometallics 2005, 24, 2831-2833.
-
(2005)
Organometallics
, vol.24
, pp. 2831-2833
-
-
Grundl, M.A.1
Kennedy-Smith, J.J.2
Trauner, D.3
-
38
-
-
33845283500
-
-
Kahn, S. D.; Pau, C. F.; Chamberlin, A. R.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 650-663.
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 650-663
-
-
Kahn, S.D.1
Pau, C.F.2
Chamberlin, A.R.3
Hehre, W.J.4
-
42
-
-
77949385732
-
-
starcingmaterial) × 100%] provides a convenient method of describing the conservation of configurational purity for a reaction.
-
starcingmaterial) × 100%] provides a convenient method of describing the conservation of configurational purity for a reaction.
-
-
-
-
44
-
-
0000749009
-
-
(b) Goering, H. L.; Kantner, S. S.; Tseng, C. C. J. Org. Chem. 1983, 48, 715-721.
-
(1983)
J. Org. Chem.
, vol.48
, pp. 715-721
-
-
Goering, H.L.1
Kantner, S.S.2
Tseng, C.C.3
-
49
-
-
33947464450
-
-
(26)(a) Speier, J. L.; Webster, J. A.; Barnes, G. H. J. Am. Chem. Soc. 1957, 79, 974-979.
-
(1957)
J. Am. Chem. Soc.
, vol.79
, pp. 974-979
-
-
Speier, J.L.1
Webster, J.A.2
Barnes, G.H.3
-
50
-
-
0001042606
-
-
(b) Chandra, G.; Lo, P. Y.; Hitchcock, P. B.; Lappert, M. F. Organometallics 1987, 6, 191-192.
-
(1987)
Organometallics
, vol.6
, pp. 191-192
-
-
Chandra, G.1
Lo, P.Y.2
Hitchcock, P.B.3
Lappert, M.F.4
-
52
-
-
77949362392
-
-
N2′ reaction of Grignard reagents with allylic carbamates; see ref 23d. However, the stereochemical identity and purity of the α-substituted allylic silanol was too important to be assumed from analogous precedent.
-
N2′ reaction of Grignard reagents with allylic carbamates; see ref 23d. However, the stereochemical identity and purity of the α-substituted allylic silanol was too important to be assumed from analogous precedent.
-
-
-
-
53
-
-
50549172591
-
-
(29)(a) Corey, E. J.; Mock, W. L.; Pasto, D. J. Tetrahedron Lett. 1961, 11, 347-352.
-
(1961)
Tetrahedron Lett.
, vol.11
, pp. 347-352
-
-
Corey, E.J.1
Mock, W.L.2
Pasto, D.J.3
-
54
-
-
84995182493
-
-
(b) Hünig, S.; Müller, H. R. Angew. Chem., Int. Ed. Engl. 1962, 1, 213-214.
-
(1962)
Angew. Chem., Int. Ed. Engl.
, vol.1
, pp. 213-214
-
-
Hünig, S.1
Müller, H.R.2
-
55
-
-
3643127470
-
-
(30)(a) Fleming, L; Henning, R.; Plaut, H. J. Chem. Soc., Chem. Commun. 1984, 29-31.
-
(1984)
J. Chem. Soc., Chem. Commun.
, pp. 29-31
-
-
Fleming, L.1
Henning, R.2
Plaut, H.3
-
56
-
-
0000276453
-
-
(b) Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694-1696.
-
(1983)
Organometallics
, vol.2
, pp. 1694-1696
-
-
Tamao, K.1
Ishida, N.2
Tanaka, T.3
Kumada, M.4
-
58
-
-
33748974985
-
-
22 + 13.3 (c = 1.1, MeOH); see
-
22 + 13.3 (c = 1.1, MeOH); see: Takenaka, M.; Takikawa, H.; Mori, K. Liebigs Ann. 1996, 1963-1964.
-
(1996)
Liebigs Ann.
, pp. 1963-1964
-
-
Takenaka, M.1
Takikawa, H.2
Mori, K.3
-
59
-
-
77949395888
-
-
- was used for cross-coupling optimization and was synthesized by a similar route using racemic 13.
-
- was used for cross-coupling optimization and was synthesized by a similar route using racemic 13.
-
-
-
-
60
-
-
77949351220
-
-
The crotylation of bromobenzene with sodium 2-butenyldimethylsilanolate under these conditions provides high γ-selectivity (26:1) as determined by GC/MS analysis of the crude reaction mixture. See ref 15.
-
The crotylation of bromobenzene with sodium 2-butenyldimethylsilanolate under these conditions provides high γ-selectivity (26:1) as determined by GC/MS analysis of the crude reaction mixture. See ref 15.
-
-
-
-
61
-
-
10144222904
-
-
(35)(a) Fairlamb, I. J. S.; Kapdi, A. R.; Lee, A. F. Org. Lett. 2004, 6, 4435-4438.
-
(2004)
Org. Lett.
, vol.6
, pp. 4435-4438
-
-
Fairlamb, I.J.S.1
Kapdi, A.R.2
Lee, A.F.3
-
63
-
-
47049124845
-
-
Kiyotsuka, Y.; Acharya, H. P.; Katayama, Y.; Hyodo, T.; Kobayashi, Y. Org. Lett. 2008, 10, 1719-1722.
-
(2008)
Org. Lett.
, vol.10
, pp. 1719-1722
-
-
Kiyotsuka, Y.1
Acharya, H.P.2
Katayama, Y.3
Hyodo, T.4
Kobayashi, Y.5
-
64
-
-
77949374132
-
-
Menicagli, R.; Piccolo, O.; Lardicci, L. Chim. Ind. 1975, 57, 499-500.
-
(1975)
Chim. Ind.
, vol.57
, pp. 499-500
-
-
Menicagli, R.1
Piccolo, O.2
Lardicci, L.3
-
65
-
-
0042478256
-
-
Lebibi, J.; Pelinski, L.; Maciejewski, L.; Brocard, J. Tetrahedron 1990, 46, 6011-6020.
-
(1990)
Tetrahedron
, vol.46
, pp. 6011-6020
-
-
Lebibi, J.1
Pelinski, L.2
Maciejewski, L.3
Brocard, J.4
-
66
-
-
0034693307
-
-
Spino, C.; Beaulieu, C.; Lafreniere, J. J. Org. Chem. 2000, 65, 7091-7097.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 7091-7097
-
-
Spino, C.1
Beaulieu, C.2
Lafreniere, J.3
-
68
-
-
77949355486
-
-
0C, 69% yield (5.2:1 E-γ/α.).
-
0C, 69% yield (5.2:1 E-γ/α.).
-
-
-
-
69
-
-
77949386515
-
-
By analogy, the absolute configurations of 23b, 20f, and 23h are assigned as S, R, and S, respectively.
-
By analogy, the absolute configurations of 23b, 20f, and 23h are assigned as S, R, and S, respectively.
-
-
-
-
70
-
-
77949417344
-
-
- has the secondary effect of removing the contribution of the minor enantiomer to the product mixture; see refs 23c, d.
-
- has the secondary effect of removing the contribution of the minor enantiomer to the product mixture; see refs 23c, d.
-
-
-
-
74
-
-
34247121057
-
-
In other closed, transition-state structures of palladium-catalyzed allylations, the vinylic methyl group positioned coplanar with the square plane of palladium ligands was suggested to be disfavored. See: Iwasaki, M.; Hayashi, S.; Hirano, K.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2007, 129, 4463-4469.
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 4463-4469
-
-
Iwasaki, M.1
Hayashi, S.2
Hirano, K.3
Yorimitsu, H.4
Oshima, K.5
|