-
1
-
-
75749104737
-
-
Baylis, A. B.; Hillman, M. E. D. Ger. Offen. 1972, 2,155,113
-
(a) Baylis, A. B.; Hillman, M. E. D. Ger. Offen. 1972, 2,155,113;
-
-
-
-
2
-
-
4243830773
-
-
Chem. Abstr. 1972, 77, 34174q.
-
(1972)
Chem. Abstr.
, vol.77
-
-
-
3
-
-
75749112625
-
-
U.S. Patent 3,743,669
-
Hillman, M. E. D., Baylis, A. B. U.S. Patent 1973, 3,743,669.
-
(1973)
-
-
Hillman, M.E.D.1
Baylis, A.B.2
-
4
-
-
0001461985
-
-
(b) Morita, K.; Suzuki, Z.; Hirose, H. Bull. Chem. Soc. Jpn. 1968, 41, 2815-2819.
-
(1968)
Bull. Chem. Soc. Jpn.
, vol.41
, pp. 2815-2819
-
-
Morita, K.1
Suzuki, Z.2
Hirose, H.3
-
5
-
-
5144227748
-
-
American Cyanamid Co. U.S. Patent 1963, 3074999
-
(c) Rauhunt, M.; Currier, H. Chem. Abstr. 1963, 58, 11224a; American Cyanamid Co. U.S. Patent 1963, 3074999.
-
(1963)
Chem. Abstr.
, vol.58
-
-
Rauhunt, M.1
Currier, H.2
-
9
-
-
34548185871
-
-
(d) Basavaiah, D.; Rao, K. V.; Reddy., R. J. Chem. Soc. Rev. 2007, 64, 1581-1588.
-
(2007)
Chem. Soc. Rev.
, vol.64
, pp. 1581-1588
-
-
Basavaiah, D.1
Rao, K.V.2
Reddy, R.J.3
-
10
-
-
0037366617
-
-
(e) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811-891.
-
(2003)
Chem. Rev.
, vol.103
, pp. 811-891
-
-
Basavaiah, D.1
Rao, A.J.2
Satyanarayana, T.3
-
12
-
-
0000892247
-
-
Paquette, L. A., Ed.; Wiley: NewYork
-
(g) Ciganek, E. In Organic Reactions; The catalyzed R-hydroxyalkylation and R-aminoalkylation of activated olefins (The Morita-Baylis-Hillman reaction); Paquette, L. A., Ed.; Wiley: NewYork, 1997; Vol.51, p 201.
-
(1997)
Organic Reactions; The Catalyzed R-hydroxyalkylation and R-aminoalkylation of Activated Olefins (The Morita-Baylis-Hillman Reaction)
, vol.51
, pp. 201
-
-
Ciganek, E.1
-
14
-
-
38049086667
-
-
For recent asymmetric MBH reactions, see: (a) Tang, H.; Zhao, G.; Zhou, Z.; Gao, P.; He, L.; Tang, C. Eur. J. Org. Chem. 2008, 126-135.
-
(2008)
Eur. J. Org. Chem.
, pp. 126-135
-
-
Tang, H.1
Zhao, G.2
Zhou, Z.3
Gao, P.4
He, L.5
Tang, C.6
-
15
-
-
53849139112
-
-
(b) Gruttadauria, M.; Giacalone, F.; Lo Meo, P.; Masculescu, A. M.; Riela, S.; Noto, R. Eur. J. Org. Chem. 2008, 1589-1596.
-
(2008)
Eur. J. Org. Chem.
, pp. 1589-1596
-
-
Gruttadauria, M.1
Giacalone, F.2
Lo Meo, P.3
Masculescu, A.M.4
Riela, S.5
Noto, R.6
-
17
-
-
34347262098
-
-
(d) Masson, G.; Housseman, C.; Zhu, J. Angew. Chem., Int. Ed. 2007, 46, 4614-4628.
-
(2007)
Angew. Chem., Int. Ed.
, vol.46
, pp. 4614-4628
-
-
Masson, G.1
Housseman, C.2
Zhu, J.3
-
18
-
-
33748989516
-
-
(e) Berkessel, A.; Roland, K.; Neudorfl, M. J. Org. Lett. 2006, 8, 4195-4198.
-
(2006)
Org. Lett.
, vol.8
, pp. 4195-4198
-
-
Berkessel, A.1
Roland, K.2
Neudorfl, M.J.3
-
19
-
-
33845270124
-
-
(f) Nakano, A.; Takahashi, K.; Hatakeyama, S. Org. Lett. 2006, 8, 5357-5360.
-
(2006)
Org. Lett.
, vol.8
, pp. 5357-5360
-
-
Nakano, A.1
Takahashi, K.2
Hatakeyama, S.3
-
20
-
-
15744396095
-
-
(g) Matsui, K.; Takizawa, S.; Sasai, H. J. Am. Chem. Soc. 2005, 127, 3680-3681,
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 3680-3681
-
-
Matsui, K.1
Takizawa, S.2
Sasai, H.3
-
22
-
-
70249113777
-
-
For recent mechanistic studies, see: (a) Roy, D.; Patel, C.; Sunoj, R. B. J. Org. Chem. 2009, 74, 6936-6943.
-
(2009)
J. Org. Chem.
, vol.74
, pp. 6936-6943
-
-
Roy, D.1
Patel, C.2
Sunoj, R.B.3
-
23
-
-
17044437071
-
-
(b) Aggarwal, V. K.; Fulford, S. Y.; Lloyd-Jones, G. C. Angew. Chem., Int. Ed. 2005, 44, 1706-1708.
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 1706-1708
-
-
Aggarwal, V.K.1
Fulford, S.Y.2
Lloyd-Jones, G.C.3
-
24
-
-
4544278079
-
-
(c) Santos, L. S.; Pavam, C. H.; Almeida, W. P.; Coelho, F.; Eberlin, M. N. Angew. Chem., Int. Ed. 2004, 43, 4330-4333.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 4330-4333
-
-
Santos, L.S.1
Pavam, C.H.2
Almeida, W.P.3
Coelho, F.4
Eberlin, M.N.5
-
25
-
-
18744378020
-
-
(d) Price, K. E.; Broadwater, S. J.; Walker, B. J.; McQuade, D. T. J. Org. Chem. 2005, 70, 3980-3987.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 3980-3987
-
-
Price, K.E.1
Broadwater, S.J.2
Walker, B.J.3
McQuade, D.T.4
-
27
-
-
0000519434
-
-
(b) Balei, M.; Sutbeyaz, Y.; Secen, H. Tetrahedron 1990, 46, 3715-3742.
-
(1990)
Tetrahedron
, vol.46
, pp. 3715-3742
-
-
Balei, M.1
Sutbeyaz, Y.2
Secen, H.3
-
28
-
-
1842587810
-
-
(c) Magdziak, D.; Meek, S. J.; Pettus, T. R. R. Chem. Rev. 2004, 104, 1383-1429.
-
(2004)
Chem. Rev.
, vol.104
, pp. 1383-1429
-
-
Magdziak, D.1
Meek, S.J.2
Pettus, T.R.R.3
-
29
-
-
4344612772
-
-
(d) Marco-Contelles, J.; Molina, M. T.; Anjum, S. Chem. Rev. 2004, 104, 2857-2899.
-
(2004)
Chem. Rev.
, vol.104
, pp. 2857-2899
-
-
Marco-Contelles, J.1
Molina, M.T.2
Anjum, S.3
-
30
-
-
18844450218
-
-
(e) Wang, X.; Porco, J. A. Angew. Chem., Int. Ed. 2005, 44, 3067-3071.
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 3067-3071
-
-
Wang, X.1
Porco, J.A.2
-
31
-
-
13644270368
-
-
(f) Baldwin, J. E.; Adlington, R. M.; Sham, V. W.-W.; Márquez, R.; Bulger, P. G. Tetrahedron 2005, 61, 2353-2363.
-
(2005)
Tetrahedron
, vol.61
, pp. 2353-2363
-
-
Baldwin, J.E.1
Adlington, R.M.2
Sham, V.W.-W.3
Márquez, R.4
Bulger, P.G.5
-
32
-
-
12344254823
-
-
(a) Berry, J. M.; Bradshaw, T. D.; Fichtner, I.; Ren, R.; Schwalbe, C H.; Wells, G.; Chew, E.-H.; Stevens, M. F. G.; Westwell, A. D. J. Med. Chem. 2005, 48, 639-644.
-
(2005)
J. Med. Chem.
, vol.48
, pp. 639-644
-
-
Berry, J.M.1
Bradshaw, T.D.2
Fichtner, I.3
Ren, R.4
Schwalbe, C.H.5
Wells, G.6
Chew, E.-H.7
Stevens, M.F.G.8
Westwell, A.D.9
-
33
-
-
0037434507
-
-
(b) Wells, G.; Berry, J. M.; Bradshaw, T. D.; Burger, A. M.; Seaton, A.; Wang, B.; Westwell, A. D.; Stevens, M. F. G. J. Med. Chem. 2003, 46, 532-541.
-
(2003)
J. Med. Chem.
, vol.46
, pp. 532-541
-
-
Wells, G.1
Berry, J.M.2
Bradshaw, T.D.3
Burger, A.M.4
Seaton, A.5
Wang, B.6
Westwell, A.D.7
Stevens, M.F.G.8
-
34
-
-
33746211332
-
-
(a) Carreño, M. C.; González-López, M.; Urbano, A. Angew. Chem., Int. Ed. 2006, 45, 2737-2741.
-
(2006)
Angew. Chem., Int. Ed.
, vol.45
, pp. 2737-2741
-
-
Carreño, M.C.1
González-López, M.2
Urbano, A.3
-
35
-
-
36849014341
-
-
(b) Barradas, S.; Carreño, M. C.; González-López, M.; Urbano, A. Org. Lett. 2007, 46, 5019-5022.
-
(2007)
Org. Lett.
, vol.46
, pp. 5019-5022
-
-
Barradas, S.1
Carreño, M.C.2
González-López, M.3
Urbano, A.4
-
36
-
-
70349280229
-
-
(c) Barradas, S.; Urbano, A.; Carreño, M. C. Chem.-Eur. J. 2009, 15, 9286-9289.
-
(2009)
Chem.-Eur. J.
, vol.15
, pp. 9286-9289
-
-
Barradas, S.1
Urbano, A.2
Carreño, M.C.3
-
37
-
-
33846416531
-
-
For recent synthetic applications of p-[(p-tolylsulfinyl)methyl]-p- quinols, see: Carreño, M. C.; Somoza, A.; Ribagorda, M.; Urbano, A. Chem.-Eur. J. 2007, 13, 879-890.
-
(2007)
Chem.-Eur. J.
, vol.13
, pp. 879-890
-
-
Carreño, M.C.1
Somoza, A.2
Ribagorda, M.3
Urbano, A.4
-
38
-
-
33846615903
-
-
(b) Carreño, M. C.; Merino, E.; Ribagorda, M.; Somoza, A.; Urbano, A. Chem-Eur. J. 2007, 13, 1064-1077.
-
(2007)
Chem-Eur. J.
, vol.13
, pp. 1064-1077
-
-
Carreño, M.C.1
Merino, E.2
Ribagorda, M.3
Somoza, A.4
Urbano, A.5
-
39
-
-
70349924940
-
-
(c) For a recent overview of our work, see: Carreño, M. C.; Hernández-Torres, G.; Ribagorda, M.; Urbano, A. Chem. Commun. 2009, 6129-6144.
-
(2009)
Chem. Commun.
, pp. 6129-6144
-
-
Carreño, M.C.1
Hernández-Torres, G.2
Ribagorda, M.3
Urbano, A.4
-
40
-
-
26444470448
-
-
(a) Adam, W.; Kazakov, D. V.; Kazakov, V. P. Chem. Rev. 2005, 105, 3371-3387.
-
(2005)
Chem. Rev.
, vol.105
, pp. 3371-3387
-
-
Adam, W.1
Kazakov, D.V.2
Kazakov, V.P.3
-
43
-
-
75749092688
-
-
5, unit cell parameters a = 7.58380(10) Å, b = 17.6558(6) Å, c = 9.6242(3) Å, β = 98.371(2)°, space group P21/c. For details, see the Supporting Information
-
5, unit cell parameters a = 7.58380(10) Å, b = 17.6558(6) Å, c = 9.6242(3) Å, β = 98.371(2)°, space group P21/c. For details, see the Supporting Information.
-
-
-
-
44
-
-
0004803217
-
-
For the synthesis of similar dioxolanes via acid-catalyzed reactions of p-benzo- and p-naphthoquinols with aliphatic aldehydes, see: Jefford, C. W.; Rossier, J.-C.; Kohomoto S.; Boukouvalas, J. Synthesis 1985, 29-31.
-
(1985)
Synthesis
, pp. 29-31
-
-
Jefford, C.W.1
Rossier, J.-C.2
Kohomoto, S.3
Boukouvalas, J.4
-
46
-
-
0034968512
-
-
(b) Watanabe, H.; Machida, K.; Nagatsuka, H.; Kitahara, T. Chirality 2001, 13, 379-385.
-
(2001)
Chirality
, vol.13
, pp. 379-385
-
-
Watanabe, H.1
Machida, K.2
Nagatsuka, H.3
Kitahara, T.4
-
48
-
-
0001656341
-
-
Carreño, M. C.; Pérez-González, M.; Ribagaorda, M.; Houk, K. N. J. Org. Chem. 1998, 63, 3687-3693.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 3687-3693
-
-
Carreño, M.C.1
Pérez-González, M.2
Ribagaorda, M.3
Houk, K.N.4
-
49
-
-
75749095684
-
-
Similar approaches to the re-face of the aldehyde would give the same mixture of diastereomers with the opposite configurations
-
Similar approaches to the re-face of the aldehyde would give the same mixture of diastereomers with the opposite configurations.
-
-
-
-
50
-
-
37849014325
-
-
(a) Robiette, R.; Aggarwal, V. K.; Harvey, J. N. J. Am. Chem. Soc. 2007, 129, 15513-15525.
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 15513-15525
-
-
Robiette, R.1
Aggarwal, V.K.2
Harvey, J.N.3
-
51
-
-
33847414560
-
-
(b) Park, K.-S.; Kim, J.; Choo, H.; Chong, Y. Synlett 2007, 3, 395-398.
-
(2007)
Synlett
, vol.3
, pp. 395-398
-
-
Park, K.-S.1
Kim, J.2
Choo, H.3
Chong, Y.4
-
52
-
-
0013308184
-
-
(c) Cai, J.; Zhou, Z.; Tang, C. Org. Lett. 2002, 4, 4723-4725.
-
(2002)
Org. Lett.
, vol.4
, pp. 4723-4725
-
-
Cai, J.1
Zhou, Z.2
Tang, C.3
-
53
-
-
0037169021
-
-
(d) Aggarwal, V. K.; Fean, D. K.; Mereu, A.; Williams, R. J. Org. Chem. 2002, 67, 510-514.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 510-514
-
-
Aggarwal, V.K.1
Fean, D.K.2
Mereu, A.3
Williams, R.4
-
54
-
-
0037037978
-
-
(e) Luo, S.; Zhang, B.; He, J.; Janczuk, A.; Wang, P. G.; Cheng, J.-P. Tetrahedron Lett. 2002, 43, 7369-7371.
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 7369-7371
-
-
Luo, S.1
Zhang, B.2
He, J.3
Janczuk, A.4
Wang, P.G.5
Cheng, J.-P.6
-
55
-
-
0035838860
-
-
(f) Yu, C.; Liu, B.; Hu, L. J. Org. Chem. 2001, 6, 5413-5418.
-
(2001)
J. Org. Chem.
, vol.6
, pp. 5413-5418
-
-
Yu, C.1
Liu, B.2
Hu, L.3
-
57
-
-
0027974067
-
-
(h) Auge, J.; Lubin, N.; Lubineau, A. Tetrahedron Lett. 1994, 35, 7947-7948.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 7947-7948
-
-
Auge, J.1
Lubin, N.2
Lubineau, A.3
-
58
-
-
84948256942
-
-
(i) Ameer, F.; Drewes, S. E.; Freese, S.; Kaye, P. T. Synth. Commun. 1998, 18, 495-500.
-
(1998)
Synth. Commun.
, vol.18
, pp. 495-500
-
-
Ameer, F.1
Drewes, S.E.2
Freese, S.3
Kaye, P.T.4
-
59
-
-
75749154116
-
-
5, unit cell parameters a = 6.9945(3) Å, b = 8.7663(6) Å, c = 10.6230(6) Å, α = 101.662(3)°, β = 98.586(3)°, γ = 91.319(3)°, space group P-1. For details, see the Supporting Information
-
5, unit cell parameters a = 6.9945(3) Å, b = 8.7663(6) Å, c = 10.6230(6) Å, α = 101.662(3)°, β = 98.586(3)°, γ = 91.319(3)°, space group P-1. For details, see the Supporting Information.
-
-
-
-
60
-
-
0001107683
-
-
(a) Imagawa, T.; Uemura, K.; Nagai, Z.; Kawanishi, M. Synth Commun. 1984, 14, 1267-1273.
-
(1984)
Synth Commun.
, vol.14
, pp. 1267-1273
-
-
Imagawa, T.1
Uemura, K.2
Nagai, Z.3
Kawanishi, M.4
-
61
-
-
0000516236
-
-
(b) Aggarwal, V. K.; Mereu, A.; Tarver, G. J.; McCague, R. J. Org. Chem. 1998, 63, 7183-7189.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 7183-7189
-
-
Aggarwal, V.K.1
Mereu, A.2
Tarver, G.J.3
McCague, R.4
-
64
-
-
75749111450
-
-
Using MeOH as solvent reaction was sluggish, and double MBH adducts were obatined in low yields
-
Using MeOH as solvent reaction was sluggish, and double MBH adducts were obatined in low yields.
-
-
-
-
65
-
-
75749116833
-
-
4, a = 8.3330(6) Å, b = 22.7385(15) Å, c = 10.3520(7) Å, β = 105.193(4)°, space group P21/n. For details, see the Supporting Information
-
4, a = 8.3330(6) Å, b = 22.7385(15) Å, c = 10.3520(7) Å, β = 105.193(4)°, space group P21/n. For details, see the Supporting Information.
-
-
-
-
67
-
-
75749137414
-
-
3, yielded the fused bicyclic ketal derivative 3a
-
3, yielded the fused bicyclic ketal derivative 3a.
-
-
-
-
68
-
-
0042449834
-
-
For examples of MBH reaction intermolecularly catalyzed by oxygen nucleophiles, see: (a) Ciganek, E. J. Org. Chem. 1995, 60, 4635-4637.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 4635-4637
-
-
Ciganek, E.1
-
69
-
-
9344229267
-
-
See also ref 2b
-
(b) Luo, S.; Mi, X.; Wang, P. G.; Cheng, J.-P. J. Org. Chem. 2004, 69, 8413-8422. See also ref 2b.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 8413-8422
-
-
Luo, S.1
Mi, X.2
Wang, P.G.3
Cheng, J.-P.4
-
70
-
-
2942696621
-
-
For an example of oxa-Michael/aldol-type condensation process, see: Lesch, B.; Bräse, S. Angew. Chem., Int. Ed. 2004, 43, 115-118.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 115-118
-
-
Lesch, B.1
Bräse, S.2
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