-
1
-
-
0012397313
-
-
For reviews, see: (a) Snieckus, V. Chem. Rev. 1990, 90, 879-933.
-
(1990)
Chem. Rev.
, vol.90
, pp. 879-933
-
-
Snieckus, V.1
-
2
-
-
0141713788
-
-
Astruc, D., Ed.; Wiley-VCH: Weinheim, Germany
-
(b) Härtung, C. G.; Snieckus, V. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: Weinheim, Germany, 2002; pp 330-367.
-
(2002)
Modern Arene Chemistry
, pp. 330-367
-
-
Härtung, C.G.1
Snieckus, V.2
-
3
-
-
22244435422
-
-
Rappoport, Z., Marek, I., Eds.; Wiley: Chichester, U.K.
-
(c) Clayden, J. In The Chemistry of Organolithium Compounds; Rappoport, Z., Marek, I., Eds.; Wiley: Chichester, U.K., 2004; pp 495-646.
-
(2004)
The Chemistry of Organolithium Compounds
, pp. 495-646
-
-
Clayden, J.1
-
4
-
-
3242659209
-
-
For mechanistic aspects, especially related to the influence of the Complex Induced Proximity Effect (CIPE), see: (d) Whislet, M. C.; MacNeil, S.; Snieckus, V.; Beak, P. Angew. Chem., Int. Ed. 2004, 43, 2206-2225.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 2206-2225
-
-
Whislet, M.C.1
MacNeil, S.2
Snieckus, V.3
Beak, P.4
-
6
-
-
0004219714
-
-
Schlosser, M., Ed.; Wiley: Chichester, U.K.
-
(b) Schlosser, M. In Organometallics in Synthesis, 2nd ed.; Schlosser, M., Ed.; Wiley: Chichester, U.K., 2002; pp 1-352. See also ref 1c.
-
(2002)
Organometallics in Synthesis, 2nd Ed.
, pp. 1-352
-
-
Schlosser, M.1
-
7
-
-
84948500445
-
-
Christensen, H. Synth. Commun. 1975, 5, 65-78. For further examples, see ref 2.
-
(1975)
Synth. Commun.
, vol.5
, pp. 65-78
-
-
Christensen, H.1
-
9
-
-
0001207373
-
-
Side product formation by this rearrangement may be avoided in certain cases by using lower reaction temperatures; for an example, see: (a) Wang, W.; Snieckus, V. J. Org. Chem. 1992, 57, 424-426.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 424-426
-
-
Wang, W.1
Snieckus, V.2
-
10
-
-
0013463085
-
-
(b) van Doorn, A. R.; Bos, M.; Harkema, S.; van Eerden, J.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1991, 56, 2371-2380.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 2371-2380
-
-
Van Doorn, A.R.1
Bos, M.2
Harkema, S.3
Van Eerden, J.4
Verboom, W.5
Reinhoudt, D.N.6
-
11
-
-
0000708518
-
-
For synthetic applications of the anionic ortho-Fries rearrangement and other O → C carbamoyl transfer reactions, see ref 5a and: (a) Kalinin, A. V.; Miah, M. A. J.; Chattopadhyay, S.; Tsukazaki, M.; Wicki, M.; Nguen, T.; Coelho, A. L.; Kerr, M.; Snieckus, V. Synlett 1997, 839-841.
-
(1997)
Synlett
, pp. 839-841
-
-
Kalinin, A.V.1
Miah, M.A.J.2
Chattopadhyay, S.3
Tsukazaki, M.4
Wicki, M.5
Nguen, T.6
Coelho, A.L.7
Kerr, M.8
Snieckus, V.9
-
12
-
-
0030819305
-
-
(b) Mohri, S.-i.; Stefinovic, M.; Snieckus, V. J. Org. Chem. 1997, 62, 7072-7073.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 7072-7073
-
-
Mohri, S.-I.1
Stefinovic, M.2
Snieckus, V.3
-
13
-
-
0032500061
-
-
(c) Kalinin, A. V.; da Silva, A. J. M.; Lopes, C. C.; Lopes, R. S. C.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4995-4998.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 4995-4998
-
-
Kalinin, A.V.1
Da Silva, A.J.M.2
Lopes, C.C.3
Lopes, R.S.C.4
Snieckus, V.5
-
15
-
-
0033577824
-
-
(e) Chauder, B. A.; Kalinin, A. V.; Taylor, N. J.; Snieckus, V. Angew. Chem., Int. Ed. 1999, 38, 1435-1438.
-
(1999)
Angew. Chem., Int. Ed.
, vol.38
, pp. 1435-1438
-
-
Chauder, B.A.1
Kalinin, A.V.2
Taylor, N.J.3
Snieckus, V.4
-
16
-
-
3242691776
-
-
(f) Reed, M. A.; Chang, M. T.; Snieckus, V. Org. Lett. 2004, 6, 2297-2300.
-
(2004)
Org. Lett.
, vol.6
, pp. 2297-2300
-
-
Reed, M.A.1
Chang, M.T.2
Snieckus, V.3
-
17
-
-
33645591959
-
-
Unpublished results
-
2Zr(H)Cl has been developed: Morin, J.; Snieckus, V. Unpublished results.
-
-
-
Morin, J.1
Snieckus, V.2
-
18
-
-
0001491460
-
-
Metallinos, C.; Nerdinger, S.; Snieckus, V. Org. Lett. 1999, 1, 1183-1186.
-
(1999)
Org. Lett.
, vol.1
, pp. 1183-1186
-
-
Metallinos, C.1
Nerdinger, S.2
Snieckus, V.3
-
20
-
-
84985580904
-
-
Direct N,C-dilithiation of O-aryl N-monoalkylcarbamates cannot be achieved due to an irreversible cleavage reaction of the initial formed N-lithiated intermediate (see ref 9). In contrast to this observation, the analogues O-allyl and S-allyl carbamates can be converted to the dianionic species, see: (a) Hanko, R.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1981, 20, 127-128.
-
(1981)
Angew. Chem., Int. Ed. Engl.
, vol.20
, pp. 127-128
-
-
Hanko, R.1
Hoppe, D.2
-
21
-
-
0042263385
-
-
(b) Marr, F.; Fröhlich, R.; Hoppe, D. Org. Lett. 1999, 1, 2081-2083.
-
(1999)
Org. Lett.
, vol.1
, pp. 2081-2083
-
-
Marr, F.1
Fröhlich, R.2
Hoppe, D.3
-
22
-
-
0036711989
-
-
(c) Marr, F.; Fröhlich, R.; Wibbeling, B.; Diedrich, C.; Hoppe, D. Eur. J. Org. Chem. 2002, 2970-2988.
-
(2002)
Eur. J. Org. Chem.
, pp. 2970-2988
-
-
Marr, F.1
Fröhlich, R.2
Wibbeling, B.3
Diedrich, C.4
Hoppe, D.5
-
23
-
-
33645605481
-
-
Müller, E., Ed.; Thieme: Stuttgart, Germany
-
(a) Petersen, S. In Methoden der Organischen Chemie (Hauben-Weyl), 4th ed.; Müller, E., Ed.; Thieme: Stuttgart, Germany, 1956; Vol. VIII, pp 137-149.
-
(1956)
Methoden der Organischen Chemie (Hauben-Weyl), 4th Ed.
, vol.8
, pp. 137-149
-
-
Petersen, S.1
-
24
-
-
0014243185
-
-
The N-monoalkylcarbamoyl group has been used as protecting group for phenols of tyrosine derivatives: (b) Jäger, G.; Geiger, R.; Siedel, W. Chem. Ber. 1968, 101, 2762-2770.
-
(1968)
Chem. Ber.
, vol.101
, pp. 2762-2770
-
-
Jäger, G.1
Geiger, R.2
Siedel, W.3
-
27
-
-
0035831971
-
-
(c) Barberis, C.; Voyer, N.; Roby, J.; Chénard, S.; Tremblay, M.; Labrie, P. Tetrahedron 2001, 57, 2965-2972.
-
(2001)
Tetrahedron
, vol.57
, pp. 2965-2972
-
-
Barberis, C.1
Voyer, N.2
Roby, J.3
Chénard, S.4
Tremblay, M.5
Labrie, P.6
-
28
-
-
33645592750
-
-
note
-
Normally, the salt TMEDA-HOTf precipitates as an oil, which solidifies on cooling to -78 °C. Due to its consistency, it undergoes reaction more slowly than 3 with the alkyllithium reagent. As a result, even when applying only 1.1 equiv of butyllithium, high yields of 6 are achieved (see ref 9).
-
-
-
-
29
-
-
33645587074
-
-
note
-
The oxazinone byproduct 10 reacted under deprotection conditions C (see Table 2, entry 3) as well as carbamate 9e to the corresponding salicylic aldehyde 15c, so that a high overall yield was obtained.
-
-
-
-
30
-
-
11244296859
-
-
de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany
-
The purification and analysis of organoboronic acids are generally difficult due to their spontaneous condensation to various degrees to boroxines; for a discussion of possibilities for their derivatization and isolation, see: (a) Miyaura, N. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; pp 41-123.
-
(2004)
Metal-Catalyzed Cross-Coupling Reactions, 2nd Ed.
, pp. 41-123
-
-
Miyaura, N.1
-
31
-
-
33645596870
-
-
Köster, R., Ed.; Thieme: Stuttgart, Germany
-
See also ref 26c. For a general review on organoboronic acids and their esters, see: (b) Köster, R. In Methoden der Organischen Chemie (Houben-Weyl), 4th ed.; Köster, R., Ed.; Thieme: Stuttgart, Germany, 1982; Vol. 13/3a, pp 489-852.
-
(1982)
Methoden der Organischen Chemie (Houben-Weyl), 4th Ed.
, vol.13
, Issue.3 A
, pp. 489-852
-
-
Köster, R.1
-
33
-
-
33645585891
-
-
note
-
3 (94%) and treatment of the resulting phenol with isopropyl isocyanate (95%). The exact procedure will be published elsewhere, see ref 22.
-
-
-
-
34
-
-
0347380140
-
-
Factor, A.; Finkbeiner, H.; Jerussi, R. A.; White, D. M. J. Org. Chem. 1970, 35, 57-62.
-
(1970)
J. Org. Chem.
, vol.35
, pp. 57-62
-
-
Factor, A.1
Finkbeiner, H.2
Jerussi, R.A.3
White, D.M.4
-
35
-
-
0141885397
-
-
(a) Van Veldhuizen, J. J.; Gillingham, D. G.; Garber, S. B.; Kataoka, O.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 12502-12508.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 12502-12508
-
-
Van Veldhuizen, J.J.1
Gillingham, D.G.2
Garber, S.B.3
Kataoka, O.4
Hoveyda, A.H.5
-
36
-
-
0001486105
-
-
(b) Antonisse, M. M. G.; Snellink-Ruël, B. H. M.; Ion, A. C.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Chem. Soc., Perkin Trans. 2 1999, 1211-1218.
-
(1999)
J. Chem. Soc., Perkin Trans. 2
, pp. 1211-1218
-
-
Antonisse, M.M.G.1
Snellink-Ruël, B.H.M.2
Ion, A.C.3
Engbersen, J.F.J.4
Reinhoudt, D.N.5
-
37
-
-
1842613107
-
-
Wessely, F.; Holzer, L.; Vilcsek, H. Monatsh. Chem. 1952, 83, 1253-1273.
-
(1952)
Monatsh. Chem.
, vol.83
, pp. 1253-1273
-
-
Wessely, F.1
Holzer, L.2
Vilcsek, H.3
-
39
-
-
2042498074
-
-
Hanack, M., Ed.; Thieme: Stuttgart, Germany
-
+ synthon, see: (b) Brandsma, L. In Methoden der Organischen Chemie (Houben-Weyl), 4th ed.; Hanack, M., Ed.; Thieme: Stuttgart, Germany, 1993; Vol. E19d, pp 369-447. See also ref 1a.
-
(1993)
Methoden der Organischen Chemie (Houben-Weyl), 4th Ed.
, vol.E19D
, pp. 369-447
-
-
Brandsma, L.1
-
41
-
-
0000718373
-
-
For reviews of 1,1′-binaphthyl systems, including BINOL derivatives, see: (a) Pu, L. Chem. Rev. 1998, 98, 2405-2494.
-
(1998)
Chem. Rev.
, vol.98
, pp. 2405-2494
-
-
Pu, L.1
-
42
-
-
0042880939
-
-
(b) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155-3211.
-
(2003)
Chem. Rev.
, vol.103
, pp. 3155-3211
-
-
Chen, Y.1
Yekta, S.2
Yudin, A.K.3
-
43
-
-
0026518693
-
-
(a) Cox, P. J.; Wang, W.; Snieckus, V. Tetrahedron Lett. 1992, 33, 2253-2256.
-
(1992)
Tetrahedron Lett.
, vol.33
, pp. 2253-2256
-
-
Cox, P.J.1
Wang, W.2
Snieckus, V.3
-
44
-
-
0028113333
-
-
For lithiation reactions of the corresponding biphenyl-2,2′-diol system, see: (b) Parsons, A. S.; Garcia, J. M.; Snieckus, V. A. Tetrahedron Lett. 1994, 35, 7537-7540.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 7537-7540
-
-
Parsons, A.S.1
Garcia, J.M.2
Snieckus, V.A.3
-
45
-
-
0000233323
-
-
(a) Buisman, G. J. H.; van der Veen, L. A.; Klootwijk, A.; de Lange, W. G. J.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Vogt, D. Organometallics 1997, 16, 2929-2939.
-
(1997)
Organometallics
, vol.16
, pp. 2929-2939
-
-
Buisman, G.J.H.1
Van Der Veen, L.A.2
Klootwijk, A.3
De Lange, W.G.J.4
Kamer, P.C.J.5
Van Leeuwen, P.W.N.M.6
Vogt, D.7
-
46
-
-
0000122940
-
-
For the synthesis of (R)-28, see also: (b) Maruoka, K.; Itoh, T.; Araki, Y.; Shirasaka, T.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1988, 61, 2975-2976.
-
(1988)
Bull. Chem. Soc. Jpn.
, vol.61
, pp. 2975-2976
-
-
Maruoka, K.1
Itoh, T.2
Araki, Y.3
Shirasaka, T.4
Yamamoto, H.5
-
47
-
-
33645600138
-
-
note
-
The complete retention of chirality (≥99% ee) during the BINOL substitution was proved by HPLC analysis of (R)-25 and (R)-28, see Experimental Section.
-
-
-
-
48
-
-
0001248031
-
-
(a) Chauder, B.; Green, L.; Snieckus, V. Pure Appl. Chem. 1999, 71, 1521-1529.
-
(1999)
Pure Appl. Chem.
, vol.71
, pp. 1521-1529
-
-
Chauder, B.1
Green, L.2
Snieckus, V.3
-
50
-
-
18744384857
-
-
de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany
-
(c) Anctil, E. J.-G.; Snieckus, V. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; pp 761-813.
-
(2004)
Metal-Catalyzed Cross-Coupling Reactions, 2nd Ed.
, pp. 761-813
-
-
Anctil, E.J.-G.1
Snieckus, V.2
-
51
-
-
24144492430
-
-
de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany
-
For reviews of coupling reactions with organozinc reagents, see: (a) Negishi, E.-i.; Zeng, X.; Tan, Z.; Qian, M.; Hu, Q.; Huang, Z. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; pp 815-889.
-
(2004)
Metal-Catalyzed Cross-Coupling Reactions, 2nd Ed.
, pp. 815-889
-
-
Negishi, E.-I.1
Zeng, X.2
Tan, Z.3
Qian, M.4
Hu, Q.5
Huang, Z.6
-
52
-
-
0026458587
-
-
(b) Erdik, E. Tetrahedron 1992, 48, 9577-9648.
-
(1992)
Tetrahedron
, vol.48
, pp. 9577-9648
-
-
Erdik, E.1
-
53
-
-
0000802361
-
-
For reviews of the Stille reaction, see: (a) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652.
-
(1997)
J. Org. React.
, vol.50
, pp. 1-652
-
-
Farina, V.1
Krishnamurthy, V.2
Scott, W.3
-
54
-
-
14344266665
-
-
de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany
-
(b) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; pp 125-161.
-
(2004)
Metal-Catalyzed Cross-Coupling Reactions, 2nd Ed.
, pp. 125-161
-
-
Mitchell, T.N.1
-
56
-
-
4644349037
-
-
de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany
-
For reviews of the Heck reaction, see: (a) Bräse, S.; de Meijere, A. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; pp 217-315.
-
(2004)
Metal-Catalyzed Cross-Coupling Reactions, 2nd Ed.
, pp. 217-315
-
-
Bräse, S.1
De Meijere, A.2
-
58
-
-
0012857368
-
-
(c) Link, J. T. Org. React. 2002, 60, 157-534.
-
(2002)
Org. React.
, vol.60
, pp. 157-534
-
-
Link, J.T.1
-
59
-
-
5444275052
-
-
de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany
-
Recent reviews: (a) Marsden, J. A.; Haley, M. M. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; pp 317-394.
-
(2004)
Metal-Catalyzed Cross-Coupling Reactions, 2nd Ed.
, pp. 317-394
-
-
Marsden, J.A.1
Haley, M.M.2
-
61
-
-
33645603131
-
-
note
-
R = 35.4 min for (R)-25).
-
-
-
-
62
-
-
0029974636
-
-
(a) Mínguez, J. M.; Castellote, M. I.; Vaquero, J. J.; García-Navio, J. L.; Alvarez-Builla, J.; Castano, O.; Andrés, J. L. J. Org. Chem. 1996, 61, 4655-4665.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 4655-4665
-
-
Mínguez, J.M.1
Castellote, M.I.2
Vaquero, J.J.3
García-Navio, J.L.4
Alvarez-Builla, J.5
Castano, O.6
Andrés, J.L.7
-
63
-
-
0028943096
-
-
(b) Terrian, D. L.; Mohammad, T.; Morrison, H. J. Org. Chem. 1995, 60, 1981-1984.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 1981-1984
-
-
Terrian, D.L.1
Mohammad, T.2
Morrison, H.3
|