-
5
-
-
0033518558
-
-
(a) Richard, J. P.; Williams, G.; Gao, J. J. Am. Chem. Soc. 1999, 121, 715.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 715
-
-
Richard, J.P.1
Williams, G.2
Gao, J.3
-
6
-
-
0001501253
-
-
Snieckus, V., Ed.; JAI Press: Washington DC
-
(b) Bradamante, S.; Pagani, G. A. Advances in Carbanion Chemistry, Vol. 2; Snieckus, V., Ed.; JAI Press: Washington DC, 1996, 189.
-
(1996)
Advances in Carbanion Chemistry
, vol.2
, pp. 189
-
-
Bradamante, S.1
Pagani, G.A.2
-
8
-
-
33947090861
-
-
(d) Dayal, S. K.; Ehrenson, S.; Taft, R. W. J. Am. Chem. Soc. 1972, 94, 9113.
-
(1972)
J. Am. Chem. Soc.
, vol.94
, pp. 9113
-
-
Dayal, S.K.1
Ehrenson, S.2
Taft, R.W.3
-
11
-
-
0005558568
-
-
(a) Agami, C.; Kazakos, A.; Levisalles, J.; Sevin, A. Tetrahedron 1980, 36, 2977.
-
(1980)
Tetrahedron
, vol.36
, pp. 2977
-
-
Agami, C.1
Kazakos, A.2
Levisalles, J.3
Sevin, A.4
-
12
-
-
0018367867
-
-
(b) Agami, C.; Fadlalah, M.; Kazakos, A.; Levisalles, J. Tetrahedron 1979, 35, 969.
-
(1979)
Tetrahedron
, vol.35
, pp. 969
-
-
Agami, C.1
Fadlalah, M.2
Kazakos, A.3
Levisalles, J.4
-
14
-
-
21644461560
-
-
(a) Sobolev, A.; Vos, M.; Zuilhof, H. T.; Sarabèr, F. C. E.; Jansen, B. J. M.; de Groot, A. Arkivoc 2005, (xiv), 29.
-
(2005)
Arkivoc
, Issue.14
, pp. 29
-
-
Sobolev, A.1
Vos, M.2
Zuilhof, H.T.3
Sarabèr, F.C.E.4
Jansen, B.J.M.5
De Groot, A.6
-
15
-
-
0016373568
-
-
(b) Inubushi, Y.; Kikuchi, T.; Ibuka, T.; Tanaka, K.; Saji, I.; Tokane, K. Chem. Pharm. Bull. 1974, 22, 349.
-
(1974)
Chem. Pharm. Bull.
, vol.22
, pp. 349
-
-
Inubushi, Y.1
Kikuchi, T.2
Ibuka, T.3
Tanaka, K.4
Saji, I.5
Tokane, K.6
-
17
-
-
84982429971
-
-
Deswarte, S.; Bellec, C.; Souchay, P. Bull. Soc. Chim. Belg. 1975, 84, 321.
-
(1975)
Bull. Soc. Chim. Belg.
, vol.84
, pp. 321
-
-
Deswarte, S.1
Bellec, C.2
Souchay, P.3
-
20
-
-
0022971248
-
-
Rasmusson, G. H.; Reynolds, G. F.; Steinberg, N. G.; Walton, E.; Patel, G. F.; Liang, T.; Cascieri, M. A.; Cheung, A. H.; Brooks, J. R.; Berman, C. J. Med. Chem. 1986, 29, 2298.
-
(1986)
J. Med. Chem.
, vol.29
, pp. 2298
-
-
Rasmusson, G.H.1
Reynolds, G.F.2
Steinberg, N.G.3
Walton, E.4
Patel, G.F.5
Liang, T.6
Cascieri, M.A.7
Cheung, A.H.8
Brooks, J.R.9
Berman, C.10
-
23
-
-
84970603460
-
-
(b) Gordon, J. L. M.; Hartshorn, M. P.; Robinson, W. T.; Sies, C. W.; Wells, B. A.; Wikaira, J. L.; Wright, G. J. Aust. J. Chem. 1990, 43, 579.
-
(1990)
Aust. J. Chem.
, vol.43
, pp. 579
-
-
Gordon, J.L.M.1
Hartshorn, M.P.2
Robinson, W.T.3
Sies, C.W.4
Wells, B.A.5
Wikaira, J.L.6
Wright, G.J.7
-
24
-
-
33645417080
-
-
(c) Bourhis, M.; Goursolle, M.; Leger, J.-M. Tetrahedron Lett 1989, 30, 4665.
-
(1989)
Tetrahedron Lett
, vol.30
, pp. 4665
-
-
Bourhis, M.1
Goursolle, M.2
Leger, J.-M.3
-
25
-
-
0041590630
-
-
(d) Heinisch, G.; Holzer, W.; Nawwar, G. A. M. Monatsh. Chem. 1986, 117, 247.
-
(1986)
Monatsh. Chem.
, vol.117
, pp. 247
-
-
Heinisch, G.1
Holzer, W.2
Nawwar, G.A.M.3
-
26
-
-
0347560149
-
-
(e) Cavazza, M.; Guella, G.; Pietra, F. Helv. Chim. Acta 1988, 71, 1608.
-
(1988)
Helv. Chim. Acta
, vol.71
, pp. 1608
-
-
Cavazza, M.1
Guella, G.2
Pietra, F.3
-
27
-
-
0142119950
-
-
(f) Gillard, M.; T'Kint, C.; Sonveaux, E.; Ghosez, L. J. Am. Chem. Soc. 1979, 101, 5837.
-
(1979)
J. Am. Chem. Soc.
, vol.101
, pp. 5837
-
-
Gillard, M.1
T'Kint, C.2
Sonveaux, E.3
Ghosez, L.4
-
34
-
-
33749098262
-
-
(a) Bailey, P. D.; Collier, I. D.; Hollinshead, S. P.; Moore, M. H.; Morgan, K. M.; Smith, D. I.; Vernon, J. M. J. Chem. Soc., Perkin Trans. 1 1997, 1209.
-
(1997)
J. Chem. Soc., Perkin Trans. 1
, pp. 1209
-
-
Bailey, P.D.1
Collier, I.D.2
Hollinshead, S.P.3
Moore, M.H.4
Morgan, K.M.5
Smith, D.I.6
Vernon, J.M.7
-
37
-
-
84985284060
-
-
(d) Quast, H.; Klaubert, C. A.; Jackman, L. M.; Freyer, A. J. Chem. Ber. 1988, 121, 1801.
-
(1988)
J. Chem. Ber.
, vol.121
, pp. 1801
-
-
Quast, H.1
Klaubert, C.A.2
Jackman, L.M.3
Freyer, A.4
-
40
-
-
0023192294
-
-
(g) Toth, I.; Bozsar, G.; Szabo, L.; Baitz-Gacs, E.; Tamas, J.; Szantay, C. Liebigs Ann. Chem. 1987, 243.
-
(1987)
Liebigs Ann. Chem.
, pp. 243
-
-
Toth, I.1
Bozsar, G.2
Szabo, L.3
Baitz-Gacs, E.4
Tamas, J.5
Szantay, C.6
-
45
-
-
0029122505
-
-
(l) For the cyclization with catalytic antibodies, see: Currie, M.; Suckling, C. J.; Zhu, L.-i.; Irvine, J.; Stimson, W. H. Tetrahedron 1995, 51, 8915.
-
(1995)
Tetrahedron
, vol.51
, pp. 8915
-
-
Currie, M.1
Suckling, C.J.2
Zhu, L.-I.3
Irvine, J.4
Stimson, W.H.5
-
48
-
-
0043257082
-
-
(b) Kulp, S. S.; Fish, V. B.; Easton, N. R. Can. J. Chem. 1965, 43, 2512.
-
(1965)
Can. J. Chem.
, vol.43
, pp. 2512
-
-
Kulp, S.S.1
Fish, V.B.2
Easton, N.R.3
-
49
-
-
0004346549
-
-
(c) Kulp, S. S.; Fish, V. B.; Easton, N. R. J. Med. Chem. 1963, 6, 516.
-
(1963)
J. Med. Chem.
, vol.6
, pp. 516
-
-
Kulp, S.S.1
Fish, V.B.2
Easton, N.R.3
-
50
-
-
33645388948
-
-
Kulp, S. S.; Molnar, J.; Miller, P. J.; Herman, S. T. J. Org. Chem. 1971, 36, 2203.
-
(1971)
J. Org. Chem.
, vol.36
, pp. 2203
-
-
Kulp, S.S.1
Molnar, J.2
Miller, P.J.3
Herman, S.T.4
-
51
-
-
0034688659
-
-
(a) Kang, J.; Meissner, R. S.; Wyler, R.; De Mendoza, J.; Rebek, J. Jr. Bull. Korean Chem. Soc. 2000, 21, 221.
-
(2000)
Bull. Korean Chem. Soc.
, vol.21
, pp. 221
-
-
Kang, J.1
Meissner, R.S.2
Wyler, R.3
De Mendoza, J.4
Rebek Jr., J.5
-
52
-
-
0000222280
-
-
(b) Takaya, H.; Naota, T.; Murahashi, S.-I. J. Am. Chem. Soc. 1998, 120, 4244.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 4244
-
-
Takaya, H.1
Naota, T.2
Murahashi, S.-I.3
-
54
-
-
0025122180
-
-
(d) Mukherjee, A.; Seth, M.; Bhaduri, A. P.; Singh, S.; Chatterjee, R. K. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1990, 29, 191.
-
(1990)
Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.
, vol.29
, pp. 191
-
-
Mukherjee, A.1
Seth, M.2
Bhaduri, A.P.3
Singh, S.4
Chatterjee, R.K.5
-
55
-
-
37049074639
-
-
(e) Azzem, M. A.; Elgemeie, G. E. H.; Neguid, M. A.; Fahmy, H. M.; Elmassry, Z. M. J. Chem. Soc., Perkin Trans. 1 1990, 545.
-
(1990)
J. Chem. Soc., Perkin Trans. 1
, pp. 545
-
-
Azzem, M.A.1
Elgemeie, G.E.H.2
Neguid, M.A.3
Fahmy, H.M.4
Elmassry, Z.M.5
-
56
-
-
84985200472
-
-
(f) Kantlehner, W.; Mergen, W.; Haug, E.; Speh, P.; Kapassakalidis, J. J.; Braeuner, H.-J. Liebigs Ann. Chem. 1985, 1804.
-
(1985)
Liebigs Ann. Chem.
, pp. 1804
-
-
Kantlehner, W.1
Mergen, W.2
Haug, E.3
Speh, P.4
Kapassakalidis, J.J.5
Braeuner, H.-J.6
-
57
-
-
0000219947
-
-
(g) Luche, J. L.; Petrier, C.; Dupuy, C. Tetrahedron Lett. 1984, 25, 753.
-
(1984)
Tetrahedron Lett.
, vol.25
, pp. 753
-
-
Luche, J.L.1
Petrier, C.2
Dupuy, C.3
-
58
-
-
0007577629
-
-
(h) Shukla, J. S.; Misra, R.; Saxena, S. Acta Cienc. Indica 1981, 7, 77;
-
(1981)
Acta Cienc. Indica
, vol.7
, pp. 77
-
-
Shukla, J.S.1
Misra, R.2
Saxena, S.3
-
59
-
-
33645421423
-
-
Chem. Abstr. 1982, 97, 386626.
-
(1982)
Chem. Abstr.
, vol.97
, pp. 386626
-
-
-
62
-
-
85026874299
-
-
(a) Denmark, S. E.; Marcin, L. R.; Schnute, M. E.; Thorarensen, A. Org. Synth. 1997, 74, 33.
-
(1997)
Org. Synth.
, vol.74
, pp. 33
-
-
Denmark, S.E.1
Marcin, L.R.2
Schnute, M.E.3
Thorarensen, A.4
-
63
-
-
0024849728
-
-
(b) Lu, L.; Shoemaker, R. K.; Wheeler, D. M. S. Tetrahedron Lett. 1989, 30, 6993.
-
(1989)
Tetrahedron Lett.
, vol.30
, pp. 6993
-
-
Lu, L.1
Shoemaker, R.K.2
Wheeler, D.M.S.3
-
64
-
-
33645393065
-
-
(c) Kulp, S. S.; Schmoyer, R. W.; Freeze, D. E.; Buzas, J. J. Org. Chem. 1975, 40, 453.
-
(1975)
J. Org. Chem.
, vol.40
, pp. 453
-
-
Kulp, S.S.1
Schmoyer, R.W.2
Freeze, D.E.3
Buzas, J.4
-
65
-
-
0000666776
-
-
For an eight-membered cyclization with modest regioselectivity, see: Luyten, M.; Keese, R. Tetrahedron 1986, 42, 1687.
-
(1986)
Tetrahedron
, vol.42
, pp. 1687
-
-
Luyten, M.1
Keese, R.2
-
66
-
-
0034630966
-
-
(a) Toro, A.; Nowak, P.; Deslongchamps, P. J. Am. Chem. Soc. 2000, 122, 4526.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 4526
-
-
Toro, A.1
Nowak, P.2
Deslongchamps, P.3
-
67
-
-
0022333277
-
-
(b) Piers, E.; Abeysekera, B, F.; Herbert, D. J.; Suckling, I. D. Can. J. Chem. 1985, 63, 3418.
-
(1985)
Can. J. Chem.
, vol.63
, pp. 3418
-
-
Piers, E.1
Abeysekera, B.F.2
Herbert, D.J.3
Suckling, I.D.4
-
68
-
-
3543021019
-
-
The pKa values of ethyl acetate and acetonitrile in water are 25 (see following) and 30 (see ref. 3a), respectively: Pearson, R. G.; Dillon, R. L. J. Am. Chem. Soc. 1953, 75, 2439.
-
(1953)
J. Am. Chem. Soc.
, vol.75
, pp. 2439
-
-
Pearson, R.G.1
Dillon, R.L.2
-
70
-
-
0033834062
-
-
For recent examples of chemoselective reductions of esters in the presence of nitriles, see: (a) Banerjee, A. K.; Castillo-Melendez, J. A.; Vera, W.; Azocar, J. A.; Laya, M. S. J. Chem. Res. 2000, 324.
-
(2000)
J. Chem. Res.
, pp. 324
-
-
Banerjee, A.K.1
Castillo-Melendez, J.A.2
Vera, W.3
Azocar, J.A.4
Laya, M.S.5
-
71
-
-
0034615897
-
-
(b) Zeng, C.-M.; Han, M.; Covey, D. F. J. Org. Chem. 2000, 65, 2264.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 2264
-
-
Zeng, C.-M.1
Han, M.2
Covey, D.F.3
-
72
-
-
0037184770
-
-
Fleming, F. F.; Funk, L. A.; Altundas, R.; Sharief, V. J. Org. Chem. 2002, 67, 9414.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 9414
-
-
Fleming, F.F.1
Funk, L.A.2
Altundas, R.3
Sharief, V.4
-
82
-
-
0034685735
-
-
(c) Grossman, R. B.; Pendharkar, D. S.; Rasne, R. M.; Varner, M. A. J. Org. Chem. 2000, 65, 3255.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 3255
-
-
Grossman, R.B.1
Pendharkar, D.S.2
Rasne, R.M.3
Varner, M.A.4
-
83
-
-
0033578808
-
-
(d) Grossman, R. B.; Rasne, R. M.; Patrick, B. O. J. Org. Chem. 1999, 64, 7173.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 7173
-
-
Grossman, R.B.1
Rasne, R.M.2
Patrick, B.O.3
-
84
-
-
0033593542
-
-
(e) Grossman, R. B.; Varner, M. A.; Skaggs, A. J. J. Org. Chem. 1999, 64, 340.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 340
-
-
Grossman, R.B.1
Varner, M.A.2
Skaggs, A.J.3
-
85
-
-
0033578687
-
-
(f) Grossman, R. B.; Pendharkar, D. S.; Patrick, B. O. J. Org. Chem. 1999, 64, 7178.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 7178
-
-
Grossman, R.B.1
Pendharkar, D.S.2
Patrick, B.O.3
-
87
-
-
0000374972
-
-
(b) Xie, Z.-F.; Suemune, H.; Sakai, K. Synth. Commun. 1989, 19, 987.
-
(1989)
Synth. Commun.
, vol.19
, pp. 987
-
-
Xie, Z.-F.1
Suemune, H.2
Sakai, K.3
-
89
-
-
0000458414
-
-
(b) Coates, R. M.; Shah, S. K.; Mason, R. W. J. Am. Chem. Soc. 1979, 101, 6765.
-
(1979)
J. Am. Chem. Soc.
, vol.101
, pp. 6765
-
-
Coates, R.M.1
Shah, S.K.2
Mason, R.W.3
-
90
-
-
0001529462
-
-
(c) Banerjee, D. K.; Chatterjee, S.; Pillai, C. N.; Bhatt, M. V. J. Am. Chem. Soc. 1956, 78, 3769.
-
(1956)
J. Am. Chem. Soc.
, vol.78
, pp. 3769
-
-
Banerjee, D.K.1
Chatterjee, S.2
Pillai, C.N.3
Bhatt, M.V.4
-
93
-
-
33947479821
-
-
(f) Manson, A. J.; Sonner, F. W.; Neumann, H. C.; Christiansen, R. G.; Clarke, R. L.; Ackerman, J. H.; Page, D. F.; Dean, J. W.; Phillips, D. K.; Potts, G. O.; Arnold, A.; Beyler, A. L.; Clinton, R. O. J. Med. Chem. 1963, 6, 1.
-
(1963)
J. Med. Chem.
, vol.6
, pp. 1
-
-
Manson, A.J.1
Sonner, F.W.2
Neumann, H.C.3
Christiansen, R.G.4
Clarke, R.L.5
Ackerman, J.H.6
Page, D.F.7
Dean, J.W.8
Phillips, D.K.9
Potts, G.O.10
Arnold, A.11
Beyler, A.L.12
Clinton, R.O.13
-
94
-
-
0037601992
-
-
(a) Honda, Y.; Honda, T.; Roy, S.; Gribble, G. W. J. Org. Chem. 2003, 68, 4991.
-
(2003)
J. Org. Chem.
, vol.68
, pp. 4991
-
-
Honda, Y.1
Honda, T.2
Roy, S.3
Gribble, G.W.4
-
95
-
-
0342877828
-
-
(b) Meyer, W. L.; Huffman, R. W.; Schroeder, P. G. Tetrahedron 1968, 24, 5959.
-
(1968)
Tetrahedron
, vol.24
, pp. 5959
-
-
Meyer, W.L.1
Huffman, R.W.2
Schroeder, P.G.3
-
98
-
-
0000769756
-
-
(c) Johnson, W. S.; Petersen, J. W.; Gutsche, C. D. J. Am. Chem. Soc. 1947, 69, 2942.
-
(1947)
J. Am. Chem. Soc.
, vol.69
, pp. 2942
-
-
Johnson, W.S.1
Petersen, J.W.2
Gutsche, C.D.3
-
99
-
-
33645421865
-
-
(d) Johnson, W. S.; Petersen, J. W.; Gutsche, C. D. J. Am. Chem. Soc. 1945, 67, 2274.
-
(1945)
J. Am. Chem. Soc.
, vol.67
, pp. 2274
-
-
Johnson, W.S.1
Petersen, J.W.2
Gutsche, C.D.3
-
100
-
-
38549116906
-
Introduction of the Cyano group by substitution of metals
-
Murahashi, S.-I., Ed.; Georg Thieme: Stuttgart
-
Subramanian, L. R. Introduction of the Cyano Group by Substitution of Metals, In Science of Synthesis, Vol. 79; Murahashi, S.-I., Ed.; Georg Thieme: Stuttgart, 2004, 163.
-
(2004)
Science of Synthesis
, vol.79
, pp. 163
-
-
Subramanian, L.R.1
-
103
-
-
84985667617
-
-
Enders, D.; Pathak, V. N.; Weuster, P. Chem. Ber. 1992, 125, 515.
-
(1992)
Chem. Ber.
, vol.125
, pp. 515
-
-
Enders, D.1
Pathak, V.N.2
Weuster, P.3
-
104
-
-
0027429528
-
-
For an isolated cyanation with benzylthiocyanate, see: Krug, P.; Rudolph, A.; Weedon, A. C. Tetrahedron Lett. 1993, 34, 7221.
-
(1993)
Tetrahedron Lett.
, vol.34
, pp. 7221
-
-
Krug, P.1
Rudolph, A.2
Weedon, A.C.3
-
107
-
-
33645391381
-
-
Rodriguez, C.; Lamazouere, A.-M.; Sotiropoulos, J. C. R. Seances Acad. Sci., Ser. C 1980, 291, 179.
-
(1980)
C. R. Seances Acad. Sci., Ser. C
, vol.291
, pp. 179
-
-
Rodriguez, C.1
Lamazouere, A.-M.2
Sotiropoulos, J.3
-
108
-
-
0002000474
-
-
Tosyl cyanide is commercially available, whereas phenyl cyanate is easily synthesized: Martin, D.; Bauer, M. Org. Synth. 1982, 61, 35.
-
(1982)
Org. Synth.
, vol.61
, pp. 35
-
-
Martin, D.1
Bauer, M.2
-
112
-
-
84945114045
-
-
(c) Grigat, E.; Pütter, R.; Mühlbauer, E. Chem. Ber. 1965, 98, 3777.
-
(1965)
Chem. Ber.
, vol.98
, pp. 3777
-
-
Grigat, E.1
Pütter, R.2
Mühlbauer, E.3
-
118
-
-
1542789820
-
-
Modestly electron-rich alkenes favor a zwitterionic mechanism: (a) Gheorghiu, M. D.; Pârvulescu, L.; Drâghici, C.; Mihai, M.; Popescu, A. Rev. Roum. Chim. 1996, 41, 283.
-
(1996)
Rev. Roum. Chim.
, vol.41
, pp. 283
-
-
Gheorghiu, M.D.1
Pârvulescu, L.2
Drâghici, C.3
Mihai, M.4
Popescu, A.5
-
119
-
-
0025938515
-
-
(b) Al-Husaini, A. H.; Muqtar, M.; Ali, S. A. Tetrahedron 1991, 47, 7719.
-
(1991)
Tetrahedron
, vol.47
, pp. 7719
-
-
Al-Husaini, A.H.1
Muqtar, M.2
Ali, S.A.3
-
120
-
-
0025894158
-
-
For recent examples since previous reviews (refs. 48 and 49), see: (a) Al-Husaini, A. H.; Khan, I.; Ali, S. A. Tetrahedron 1991, 47, 3845.
-
(1991)
Tetrahedron
, vol.47
, pp. 3845
-
-
Al-Husaini, A.H.1
Khan, I.2
Ali, S.A.3
-
121
-
-
0038558280
-
-
(b) Nguyen, N. V.; Chow, K.; Moore, H. W. J. Org. Chem. 1987, 52, 1315.
-
(1987)
J. Org. Chem.
, vol.52
, pp. 1315
-
-
Nguyen, N.V.1
Chow, K.2
Moore, H.W.3
-
125
-
-
0000673580
-
-
(f) Malherbe, R.; Rist, G.; Bellus, D. J. Org. Chem. 1983, 48, 860.
-
(1983)
J. Org. Chem.
, vol.48
, pp. 860
-
-
Malherbe, R.1
Rist, G.2
Bellus, D.3
-
127
-
-
37049105141
-
-
Bamfield, H. A.; Brook, P. R.; Hunt, K. J. Chem. Soc., Chem. Commun. 1976, 146.
-
(1976)
J. Chem. Soc., Chem. Commun.
, pp. 146
-
-
Bamfield, H.A.1
Brook, P.R.2
Hunt, K.3
-
130
-
-
0034674473
-
-
Kniep, C. S.; Padias, A. B.; Hall, H. K. Jr. Tetrahedron 2000, 56, 4279.
-
(2000)
Tetrahedron
, vol.56
, pp. 4279
-
-
Kniep, C.S.1
Padias, A.B.2
Hall Jr., H.K.3
-
133
-
-
0343699054
-
-
(c) For an alternative enamine hydrolysis, see: Cobb, R. L.; Mahan, J. E. J. Org. Chem. 1977, 42, 1948.
-
(1977)
J. Org. Chem.
, vol.42
, pp. 1948
-
-
Cobb, R.L.1
Mahan, J.E.2
-
134
-
-
84982448928
-
-
Föhlisch, B.; Herter, R.; Wolf, E.; Stezowski, J. J.; Eckle, E. Chem. Ber. 1982, 115, 355.
-
(1982)
Chem. Ber.
, vol.115
, pp. 355
-
-
Föhlisch, B.1
Herter, R.2
Wolf, E.3
Stezowski, J.J.4
Eckle, E.5
-
135
-
-
6244251538
-
-
Föhlisch, B.; Herter, R.; Wolf, E. J. Chem. Res., Synop. 1986, 128.
-
(1986)
J. Chem. Res., Synop.
, pp. 128
-
-
Föhlisch, B.1
Herter, R.2
Wolf, E.3
-
136
-
-
11044226752
-
-
Habib, R.; Husain, M.; Fazal, A.; Husain, M. Indian J. Chem., Sect. B: Org. Chem. Ind. Med. Chem. 1988, 27, 584.
-
(1988)
Indian J. Chem., Sect. B: Org. Chem. Ind. Med. Chem.
, vol.27
, pp. 584
-
-
Habib, R.1
Husain, M.2
Fazal, A.3
Husain, M.4
-
137
-
-
0000119588
-
-
For a successful displacement on a five-membered oxonitrile, see: Johnson, W. S.; Anderson, J. M.; Shelberg, W. E. J. Am. Chem. Soc. 1944, 66, 218.
-
(1944)
J. Am. Chem. Soc.
, vol.66
, pp. 218
-
-
Johnson, W.S.1
Anderson, J.M.2
Shelberg, W.E.3
-
139
-
-
0037062902
-
-
(b) For a recent example, see: McComas, C. C.; Perales, J. B.; Van Vranken, D. L. Org. Lett. 2002, 4, 2337.
-
(2002)
Org. Lett.
, vol.4
, pp. 2337
-
-
McComas, C.C.1
Perales, J.B.2
Van Vranken, D.L.3
-
142
-
-
0000270719
-
-
(c) Hall, H. K. Jr.; Blanchard, E. P. Jr.; Cherkofsky, S. C.; Sieja, J. B.; Sheppard, W. A. J. Am. Chem. Soc. 1971, 93, 110.
-
(1971)
J. Am. Chem. Soc.
, vol.93
, pp. 110
-
-
Hall Jr., H.K.1
Blanchard Jr., E.P.2
Cherkofsky, S.C.3
Sieja, J.B.4
Sheppard, W.A.5
-
143
-
-
0000431050
-
-
(d) Cripps, H. N.; Williams, J. K.; Sharkey, W. H. J. Am. Chem. Soc. 1959, 81, 2723.
-
(1959)
J. Am. Chem. Soc.
, vol.81
, pp. 2723
-
-
Cripps, H.N.1
Williams, J.K.2
Sharkey, W.H.3
-
145
-
-
0032565932
-
-
Hynes, J.; Overman, L. E.; Nasser, T.; Rucker, P. V. Tetrahedron Lett. 1998, 39, 4647.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 4647
-
-
Hynes, J.1
Overman, L.E.2
Nasser, T.3
Rucker, P.V.4
-
146
-
-
0030064924
-
-
Yang, Y.; Haino, T.; Usui, S.; Fukazawa, Y. Tetrahedron 1996, 52, 2325.
-
(1996)
Tetrahedron
, vol.52
, pp. 2325
-
-
Yang, Y.1
Haino, T.2
Usui, S.3
Fukazawa, Y.4
-
147
-
-
33645385475
-
Introduction of the Cyano group by conjugate addition
-
Murahashi, S.-I., Ed.; Georg Thieme: Stuttgart
-
(a) Podlech, J. Introduction of the Cyano Group by Conjugate Addition, In Science of Synthesis, Vol. 19; Murahashi, S.-I., Ed.; Georg Thieme: Stuttgart, 2004, 311.
-
(2004)
Science of Synthesis
, vol.19
, pp. 311
-
-
Podlech, J.1
-
149
-
-
0001263254
-
-
(c) For an alternative conjugate cyanation with rerf-butyl isocyanide, see: Ito, Y.; Kato, H.; Imai, H.; Saegusa, T. J. Am. Chem. Soc. 1982, 104, 6449.
-
(1982)
J. Am. Chem. Soc.
, vol.104
, pp. 6449
-
-
Ito, Y.1
Kato, H.2
Imai, H.3
Saegusa, T.4
-
150
-
-
33645413063
-
-
note
-
A SciFinder search failed to locate any examples of additions to cyclobutenones.
-
-
-
-
151
-
-
0042734322
-
-
(a) Díez, E.; Fernández, R.; Martín-Zamora, E.; Pareja, C.; Prieto, A.; Lassalaetta, J. M. Tetrahedron: Asymmetry 1999, 10, 1145.
-
(1999)
Tetrahedron: Asymmetry
, vol.10
, pp. 1145
-
-
Díez, E.1
Fernández, R.2
Martín-Zamora, E.3
Pareja, C.4
Prieto, A.5
Lassalaetta, J.M.6
-
152
-
-
0030790372
-
-
(b) Díez, E.; Fernández, R.; Gasch, C.; Lassaletta, J. M.; Liera, J. M.; Martín-Zamora, E.; Vázquez, J. J. Org. Chem. 1997, 62, 5144.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 5144
-
-
Díez, E.1
Fernández, R.2
Gasch, C.3
Lassaletta, J.M.4
Liera, J.M.5
Martín-Zamora, E.6
Vázquez, J.7
-
153
-
-
0029931674
-
-
(c) Lassaletta, J.-M.; Fernández, R.; Martín-Zamora, E.; Díez, E. J. Am. Chem. Soc. 1996, 118, 7002.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 7002
-
-
Lassaletta, J.-M.1
Fernández, R.2
Martín-Zamora, E.3
Díez, E.4
-
156
-
-
0033590265
-
-
(b) Honda, T.; Rounds, B. V.; Bore, L.; Favaloro, F. G. Jr.; Gribble, G. W.; Suh, N.; Wang, Y.; Sporn, M. B. Bioorg. Med. Chem. Lett. 1999, 9, 3429.
-
(1999)
Bioorg. Med. Chem. Lett.
, vol.9
, pp. 3429
-
-
Honda, T.1
Rounds, B.V.2
Bore, L.3
Favaloro Jr., F.G.4
Gribble, G.W.5
Suh, N.6
Wang, Y.7
Sporn, M.B.8
-
157
-
-
0032510379
-
-
(a) Rosowsky, A.; Papoulis, A. T.; Queener, S. F. J. Med. Chem. 1998, 41, 913.
-
(1998)
J. Med. Chem.
, vol.41
, pp. 913
-
-
Rosowsky, A.1
Papoulis, A.T.2
Queener, S.F.3
-
158
-
-
0028263520
-
-
(b) Kotake, Y.; Iijima, A.; Yoshimatsu, K.; Tamai, N.; Ozawa, Y.; Koyanagi, N.; Kitoh, K.; Nomura, H. J. Med. Chem. 1994, 37, 1616.
-
(1994)
J. Med. Chem.
, vol.37
, pp. 1616
-
-
Kotake, Y.1
Iijima, A.2
Yoshimatsu, K.3
Tamai, N.4
Ozawa, Y.5
Koyanagi, N.6
Kitoh, K.7
Nomura, H.8
-
160
-
-
0035795063
-
-
Rissafi, B.; Rachiqi, N.; ElLouzi, A.; Loupy, A.; Petiti, A.; Fkih-Tétouani, S. Tetrahedron 2001, 57, 2761.
-
(2001)
Tetrahedron
, vol.57
, pp. 2761
-
-
Rissafi, B.1
Rachiqi, N.2
Ellouzi, A.3
Loupy, A.4
Petiti, A.5
Fkih-Tétouani, S.6
-
163
-
-
0033574489
-
-
(a) Fleming, F. F.; Huang, A.; Sharief, V. A.; Pu, Y. J. Org. Chem. 1999, 64, 2830.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 2830
-
-
Fleming, F.F.1
Huang, A.2
Sharief, V.A.3
Pu, Y.4
-
164
-
-
0000767933
-
-
(b) Fleming, F. P.; Huang, A.; Sharief, V. A.; Pu, Y. J. Org. Chem. 1997, 62, 3036.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 3036
-
-
Fleming, F.P.1
Huang, A.2
Sharief, V.A.3
Pu, Y.4
-
165
-
-
37049068820
-
-
(a) Haase-Held, M.; Hatzis, M.; Mann, J. J. Chem. Soc., Perkin Trans. 1 1993, 2907.
-
(1993)
J. Chem. Soc., Perkin Trans. 1
, pp. 2907
-
-
Haase-Held, M.1
Hatzis, M.2
Mann, J.3
-
166
-
-
37049067930
-
-
(b) Haase-Held, M.; Hatzis, M.; Mann, J. J. Chem. Soc., Perkin Trans. 1 1992, 2999.
-
(1992)
J. Chem. Soc., Perkin Trans. 1
, pp. 2999
-
-
Haase-Held, M.1
Hatzis, M.2
Mann, J.3
-
167
-
-
0034751735
-
-
(a) Liu, H.-J.; Ho, Y.-L.; Wu, J.-D.; Shia, K.-S. Synlett 2001, 1805.
-
(2001)
Synlett
, pp. 1805
-
-
Liu, H.-J.1
Ho, Y.-L.2
Wu, J.-D.3
Shia, K.-S.4
-
168
-
-
0035908218
-
-
(b) Wu, J.-D.; Shia, K.-S.; Liu, H.-J. Tetrahedron Lett. 2001, 42, 4207.
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 4207
-
-
Wu, J.-D.1
Shia, K.-S.2
Liu, H.-J.3
-
169
-
-
0034025671
-
-
(c) Honda, T.; Gribble, G. W.; Suh, N.; Finlay, H. J.; Rounds, B. V.; Bore, L.; Favaloro, F. G. Jr.; Wang, Y.; Sporn, M. B. J. Med. Chem. 2000, 43, 1866.
-
(2000)
J. Med. Chem.
, vol.43
, pp. 1866
-
-
Honda, T.1
Gribble, G.W.2
Suh, N.3
Finlay, H.J.4
Rounds, B.V.5
Bore, L.6
Favaloro Jr., F.G.7
Wang, Y.8
Sporn, M.B.9
-
171
-
-
0032583689
-
-
Margaretha, P.; Andresen, S. J. Photochem. Photobiol., A 1998, 112, 135.
-
(1998)
J. Photochem. Photobiol., A
, vol.112
, pp. 135
-
-
Margaretha, P.1
Andresen, S.2
-
172
-
-
0026055506
-
-
Bienfait, B.; Coppe-Motte, G.; Merényi, R.; Viehe, H. G.; Sicking, W.; Sustmann, R. Tetrahedron 1991, 47, 8167.
-
(1991)
Tetrahedron
, vol.47
, pp. 8167
-
-
Bienfait, B.1
Coppe-Motte, G.2
Merényi, R.3
Viehe, H.G.4
Sicking, W.5
Sustmann, R.6
-
176
-
-
0033233901
-
-
(a) Wang, Y.; Doering, W. v. E.; Staples, R. J. J. Chem. Crystallogr. 1999, 29, 977.
-
(1999)
J. Chem. Crystallogr.
, vol.29
, pp. 977
-
-
Wang, Y.1
Doering, W.V.E.2
Staples, R.J.3
-
183
-
-
0035939476
-
-
(c) Magnus, P.; Waring, M. J.; Olliveir, C.; Lynch, V. Tetrahedron Lett. 2001, 42, 4947.
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 4947
-
-
Magnus, P.1
Waring, M.J.2
Olliveir, C.3
Lynch, V.4
-
184
-
-
0030569322
-
-
(d) Magnus, P.; Booth, J.; Diorazio, L.; Donohoe, T.; Lynch, V.; Magnus, N.; Mendoza, J.; Pye, P.; Tarrant, J. Tetrahedron 1996, 52, 14103.
-
(1996)
Tetrahedron
, vol.52
, pp. 14103
-
-
Magnus, P.1
Booth, J.2
Diorazio, L.3
Donohoe, T.4
Lynch, V.5
Magnus, N.6
Mendoza, J.7
Pye, P.8
Tarrant, J.9
-
185
-
-
0029040730
-
-
(e) Bauta, W.; Booth, J.; Bos, M. E.; DeLuca, M.; Diorazio, L.; Donohoe, T.; Magnus, N.; Magnus, P.; Mendoza, J.; Pye, P.; Tarrant, J.; Thorn, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5327.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 5327
-
-
Bauta, W.1
Booth, J.2
Bos, M.E.3
DeLuca, M.4
Diorazio, L.5
Donohoe, T.6
Magnus, N.7
Magnus, P.8
Mendoza, J.9
Pye, P.10
Tarrant, J.11
Thorn, S.12
Ujjainwalla, F.13
-
186
-
-
0342904422
-
-
(f) Aundenaert, F.; De Keukeleire, D.; Vandewalle, M. Tetrahedron 1987, 43, 5593.
-
(1987)
Tetrahedron
, vol.43
, pp. 5593
-
-
Aundenaert, F.1
De Keukeleire, D.2
Vandewalle, M.3
-
187
-
-
0023489945
-
-
(g) Isobe, M.; Nishikawa, T.; Pikul, S.; Goto, T. Tetrahedron Lett. 1987, 28, 6485.
-
(1987)
Tetrahedron Lett.
, vol.28
, pp. 6485
-
-
Isobe, M.1
Nishikawa, T.2
Pikul, S.3
Goto, T.4
-
188
-
-
33645380229
-
-
Selenium dioxide oxidation is inefficient: Mousseron, M.; Jacquier, R.; Fontaine, A.; Zagdoun, R. Bull. Soc. Chim. Fr. 1954, 1246.
-
(1954)
Bull. Soc. Chim. Fr.
, pp. 1246
-
-
Mousseron, M.1
Jacquier, R.2
Fontaine, A.3
Zagdoun, R.4
-
189
-
-
4544304795
-
-
Fleming, F. F.; Zhang, Z.; Wang, Q.; Steward, O. W. Angew. Chem. Int. Ed. 2004, 43, 1126.
-
(2004)
Angew. Chem. Int. Ed.
, vol.43
, pp. 1126
-
-
Fleming, F.F.1
Zhang, Z.2
Wang, Q.3
Steward, O.W.4
-
191
-
-
0032238751
-
-
(a) Yang, W. Q.; Chen, S. Z.; Huang, L. Chin. Chem. Lett. 1998, 9, 233.
-
(1998)
Chin. Chem. Lett.
, vol.9
, pp. 233
-
-
Yang, W.Q.1
Chen, S.Z.2
Huang, L.3
-
192
-
-
0013332351
-
-
(b) Kuemmerie, E. W. Jr.; Rettig, T. A.; Stille, J. K. J. Org. Chem. 1975, 40, 3665.
-
(1975)
J. Org. Chem.
, vol.40
, pp. 3665
-
-
Kuemmerie Jr., E.W.1
Rettig, T.A.2
Stille, J.K.3
-
193
-
-
0037087571
-
-
Nicolaou, K. C.; Gray, D. L. F.; Montagnon, T.; Harrison, S. T. Angew. Chem. Int. Ed. 2002, 41, 996.
-
(2002)
Angew. Chem. Int. Ed.
, vol.41
, pp. 996
-
-
Nicolaou, K.C.1
Gray, D.L.F.2
Montagnon, T.3
Harrison, S.T.4
-
194
-
-
85004260121
-
-
(a) Kurihara, T.; Miki, M.; Yoneda, R.; Harusawa, S. Chem. Pharm. Bull. 1986, 34, 2747.
-
(1986)
Chem. Pharm. Bull.
, vol.34
, pp. 2747
-
-
Kurihara, T.1
Miki, M.2
Yoneda, R.3
Harusawa, S.4
-
195
-
-
0008792210
-
-
(b) Harusawa, S.; Miki, M.; Yoneda, R.; Kurihara, T. Chem. Pharm. Bull. 1985, 33, 2164.
-
(1985)
Chem. Pharm. Bull.
, vol.33
, pp. 2164
-
-
Harusawa, S.1
Miki, M.2
Yoneda, R.3
Kurihara, T.4
-
197
-
-
0033213008
-
-
A limited number of nitrile-substituted pyridones occur naturally: Fleming, F. F. Nat. Prod. Rep. 1999, 16, 597.
-
(1999)
Nat. Prod. Rep.
, vol.16
, pp. 597
-
-
Fleming, F.F.1
-
198
-
-
0004211170
-
-
Kleeman, A.; Engel, J., Eds.; Thieme: Stuttgart, 4th ed.
-
For two examples of Oxonitrile-containing' drugs, see: Milrinone lactate and Trilostane. Pharmaceutical Substances: Synthesis, Patents, Applications; Kleeman, A.; Engel, J., Eds.; Thieme: Stuttgart, 2001, 4th ed.
-
(2001)
Pharmaceutical Substances: Synthesis, Patents, Applications
-
-
-
200
-
-
84957157823
-
-
(b) Auwers, K. V.; Bahr, T.; Wegner, G.; Wiegand, C. Ber. Dtsch. Chem. Ges. 1928, 61, 408.
-
(1928)
Ber. Dtsch. Chem. Ges.
, vol.61
, pp. 408
-
-
Auwers, K.V.1
Bahr, T.2
Wegner, G.3
Wiegand, C.4
-
206
-
-
33645382941
-
-
(c) Lamant, M.; Le Guillanton, G. C. R. Seances Acad. Sci., Ser. C 1969, 268, 536.
-
(1969)
C. R. Seances Acad. Sci., Ser. C
, vol.268
, pp. 536
-
-
Lamant, M.1
Le Guillanton, G.2
-
210
-
-
84860072683
-
-
b alkylate on oxygen: (a) Susse, M.; Hájicek, J.; Hesse, M. Helv. Chim. Acta 1985, 68, 1986.
-
(1985)
Helv. Chim. Acta
, vol.68
, pp. 1986
-
-
Susse, M.1
Hájicek, J.2
Hesse, M.3
-
211
-
-
0003561552
-
-
(b) Ziegler, F. E.; Nangia, A.; Schulte, G. J. Am. Chem. Soc. 1987, 109, 3987.
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 3987
-
-
Ziegler, F.E.1
Nangia, A.2
Schulte, G.3
-
212
-
-
0004845967
-
-
Baty, J. D.; Jones, G.; Moore, C. J. Org. Chem. 1969, 34, 3295.
-
(1969)
J. Org. Chem.
, vol.34
, pp. 3295
-
-
Baty, J.D.1
Jones, G.2
Moore, C.3
-
213
-
-
0033977223
-
-
Tanaka, T.; Azuma, T.; Fang, X.; Uchida, S.; Iwata, C.; Ishida, T.; In, Y.; Maezaki, N. Synlett 2000, 33.
-
(2000)
Synlett
, pp. 33
-
-
Tanaka, T.1
Azuma, T.2
Fang, X.3
Uchida, S.4
Iwata, C.5
Ishida, T.6
In, Y.7
Maezaki, N.8
-
214
-
-
0034619644
-
-
Bailey, P. D.; Morgan, K. M.; Smith, D. I.; Vernon, J. M. J. Chem. Soc., Perkin Trans. 1 2000, 3566.
-
(2000)
J. Chem. Soc., Perkin Trans. 1
, pp. 3566
-
-
Bailey, P.D.1
Morgan, K.M.2
Smith, D.I.3
Vernon, J.M.4
-
215
-
-
0037087753
-
-
Trost, B. M.; Fraisse, P. L.; Ball, Z. T. Angew. Chem. Int. Ed. 2002, 41, 1059.
-
(2002)
Angew. Chem. Int. Ed.
, vol.41
, pp. 1059
-
-
Trost, B.M.1
Fraisse, P.L.2
Ball, Z.T.3
-
216
-
-
0032507933
-
-
Liu, H.-J.; Zhu, J.-L.; Shia, K.-S. Tetrahedron Lett. 1998, 39, 4183.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 4183
-
-
Liu, H.-J.1
Zhu, J.-L.2
Shia, K.-S.3
-
217
-
-
0014086236
-
-
Taylor, E. C.; McKillop, A.; Shvo, Y.; Hawks, G. H. Tetrahedron 1967, 23, 2081.
-
(1967)
Tetrahedron
, vol.23
, pp. 2081
-
-
Taylor, E.C.1
McKillop, A.2
Shvo, Y.3
Hawks, G.H.4
-
218
-
-
0029032398
-
-
Kotake, Y.; Okauchi, T.; Iijima, A.; Yoshimatsu, K.; Nomura, H. Chem. Pharm. Bull. 1995, 43, 829.
-
(1995)
Chem. Pharm. Bull.
, vol.43
, pp. 829
-
-
Kotake, Y.1
Okauchi, T.2
Iijima, A.3
Yoshimatsu, K.4
Nomura, H.5
-
221
-
-
84987298458
-
-
(a) Abarbri, M.; Guignard, A.; Lamant, M. Helv. Chim. Acta 1995, 78, 109.
-
(1995)
Helv. Chim. Acta
, vol.78
, pp. 109
-
-
Abarbri, M.1
Guignard, A.2
Lamant, M.3
-
222
-
-
0344574513
-
-
(b) Lamant, M.; Guignard, A. C. R. Seances Acad. Sci., Ser. C 1975, 281, 123.
-
(1975)
C. R. Seances Acad. Sci., Ser. C
, vol.281
, pp. 123
-
-
Lamant, M.1
Guignard, A.2
-
223
-
-
0026753722
-
-
Lin, H.-S.; Rampersaud, A. A.; Zimmerman, K.; Steinberg, M. I.; Boyd, D. B. J. Med. Chem. 1992, 35, 2658.
-
(1992)
J. Med. Chem.
, vol.35
, pp. 2658
-
-
Lin, H.-S.1
Rampersaud, A.A.2
Zimmerman, K.3
Steinberg, M.I.4
Boyd, D.B.5
-
225
-
-
33645415768
-
-
Cariou, M.; Lamant, M.; Normant, H. C. R. Seances Acad. Sci., Ser. C 1974, 278, 1457.
-
(1974)
C. R. Seances Acad. Sci., Ser. C
, vol.278
, pp. 1457
-
-
Cariou, M.1
Lamant, M.2
Normant, H.3
-
227
-
-
0000303827
-
-
(b) Coates, R. M.; Shah, S. K.; Mason, R. W. J. Am. Chem. Soc. 1982, 104, 2198.
-
(1982)
J. Am. Chem. Soc.
, vol.104
, pp. 2198
-
-
Coates, R.M.1
Shah, S.K.2
Mason, R.W.3
-
228
-
-
0001193489
-
-
Coates, R. M.; Rogers, B. D.; Hobbs, S. J.; Peck, D. R.; Curran, D. P. J. Am. Chem. Soc. 1987, 109, 1160.
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 1160
-
-
Coates, R.M.1
Rogers, B.D.2
Hobbs, S.J.3
Peck, D.R.4
Curran, D.P.5
-
229
-
-
0001259941
-
-
(a) Ziegler, F. E.; Metcalf, C. A. III; Nangia, A.; Schulte, G. J. Am. Chem. Soc. 1993, 115, 2581.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 2581
-
-
Ziegler, F.E.1
Metcalf III, C.A.2
Nangia, A.3
Schulte, G.4
-
230
-
-
11044229577
-
-
(b) Ziegler, F. E.; Nangia, A.; Schulte, G. Tetrahedron Lett. 1988, 29, 1669.
-
(1988)
Tetrahedron Lett.
, vol.29
, pp. 1669
-
-
Ziegler, F.E.1
Nangia, A.2
Schulte, G.3
-
231
-
-
0027321189
-
-
Enders, D.; Zamponi, A.; Raabe, G.; Runsink, J. Synthesis 1993, 725.
-
(1993)
Synthesis
, pp. 725
-
-
Enders, D.1
Zamponi, A.2
Raabe, G.3
Runsink, J.4
-
232
-
-
11044222000
-
-
For a discussion of the alkylation stereoselectivity, see: Fleming, F. F.; Zhang, Z. Tetrahedron 2005, 61, 747.
-
(2005)
Tetrahedron
, vol.61
, pp. 747
-
-
Fleming, F.F.1
Zhang, Z.2
-
234
-
-
0042903616
-
-
Debal, A.; Cuvigny, T.; Larcheveque, M. Tetrahedron Lett. 1977, 36, 3187.
-
(1977)
Tetrahedron Lett.
, vol.36
, pp. 3187
-
-
Debal, A.1
Cuvigny, T.2
Larcheveque, M.3
-
235
-
-
0012758597
-
-
The pKa values of acetonitrile and acetone are 29 (see ref. 3a) and 24, respectively: Bordwell, F. G.; Matthews, W. S. J. Am. Chem. Soc. 1974, 96, 1216.
-
(1974)
J. Am. Chem. Soc.
, vol.96
, pp. 1216
-
-
Bordwell, F.G.1
Matthews, W.S.2
-
240
-
-
84987574128
-
-
(a) Milenkov, B.; Guggisberg, A.; Hesse, M. Helv. Chim. Acta 1987, 70, 760.
-
(1987)
Helv. Chim. Acta
, vol.70
, pp. 760
-
-
Milenkov, B.1
Guggisberg, A.2
Hesse, M.3
-
242
-
-
0028826190
-
-
(c) Goulaouic-Dubois, C.; Guggisberg, A.; Hesse, M. Tetrahedron 1995, 51, 12035.
-
(1995)
Tetrahedron
, vol.51
, pp. 12035
-
-
Goulaouic-Dubois, C.1
Guggisberg, A.2
Hesse, M.3
-
244
-
-
0013072294
-
-
(b) Meyer, W. L.; Goodwin, T. E.; Hoff, R. J.; Sigel, C. W. J. Org. Chem. 1977, 42, 2761.
-
(1977)
J. Org. Chem.
, vol.42
, pp. 2761
-
-
Meyer, W.L.1
Goodwin, T.E.2
Hoff, R.J.3
Sigel, C.W.4
-
247
-
-
0041394687
-
-
Kido, F.; Noda, Y.; Yoshikoshi, A. J. Am. Chem. Soc. 1982, 104, 5509.
-
(1982)
J. Am. Chem. Soc.
, vol.104
, pp. 5509
-
-
Kido, F.1
Noda, Y.2
Yoshikoshi, A.3
-
248
-
-
1842622633
-
-
Deutsch, J.; Niclas, H.-J.; Ramm, M. J. Prakt. Chem. 1995, 337, 23.
-
(1995)
J. Prakt. Chem.
, vol.337
, pp. 23
-
-
Deutsch, J.1
Niclas, H.-J.2
Ramm, M.3
-
249
-
-
0037450403
-
-
Liu, H.-J.; Ly, T. W.; Tai, C.-L.; Wu, J.-D.; Liang, J.-K.; Guo, J.-C.; Tseng, N.-W.; Shia, K.-S. Tetrahedron 2003, 59, 1209.
-
(2003)
Tetrahedron
, vol.59
, pp. 1209
-
-
Liu, H.-J.1
Ly, T.W.2
Tai, C.-L.3
Wu, J.-D.4
Liang, J.-K.5
Guo, J.-C.6
Tseng, N.-W.7
Shia, K.-S.8
-
250
-
-
11044229336
-
-
Milenkov, B.; Süsse, M.; Hesse, M. Helv. Chim. Acta 1985, 68, 2115.
-
(1985)
Helv. Chim. Acta
, vol.68
, pp. 2115
-
-
Milenkov, B.1
Süsse, M.2
Hesse, M.3
-
251
-
-
0035124842
-
-
(a) Tai, C.-L.; Ly, T. W.; Wu, J.-D.; Shia, K.-S.; Liu, H.-J. Synlett 2001, 214.
-
(2001)
Synlett
, pp. 214
-
-
Tai, C.-L.1
Ly, T.W.2
Wu, J.-D.3
Shia, K.-S.4
Liu, H.-J.5
-
252
-
-
0035898723
-
-
(b) Olkhovik, V.; Masalov, N.; Jansen, B. J. M.; de Groot, A. Tetrahedron Lett. 2001, 42, 4903.
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 4903
-
-
Olkhovik, V.1
Masalov, N.2
Jansen, B.J.M.3
De Groot, A.4
-
256
-
-
0034737569
-
-
Jansen, B. J. M.; Hendrikx, C. C. J.; Masalov, N.; Stork, G. A.; Meulemans, T. M.; Macaev, F. Z.; de Groot, A. Tetrahedron 2000, 56, 2075.
-
(2000)
Tetrahedron
, vol.56
, pp. 2075
-
-
Jansen, B.J.M.1
Hendrikx, C.C.J.2
Masalov, N.3
Stork, G.A.4
Meulemans, T.M.5
Macaev, F.Z.6
De Groot, A.7
-
257
-
-
0030796609
-
-
Hamzaoui, M.; Provot, O.; Grégoire, F.; Riche, C.; Chiaroni, A.; Gay, F.; Moskowitz, H.; Mayrargue, J. Tetrahedron: Asymmetry 1997, 8, 2085.
-
(1997)
Tetrahedron: Asymmetry
, vol.8
, pp. 2085
-
-
Hamzaoui, M.1
Provot, O.2
Grégoire, F.3
Riche, C.4
Chiaroni, A.5
Gay, F.6
Moskowitz, H.7
Mayrargue, J.8
-
259
-
-
0027983683
-
-
Swarts, H. J.; Verstegen-Haaksma, A. A.; Jansen, B. J. M.; de Groot, A. Tetrahedron 1994, 50, 10083.
-
(1994)
Tetrahedron
, vol.50
, pp. 10083
-
-
Swarts, H.J.1
Verstegen-Haaksma, A.A.2
Jansen, B.J.M.3
De Groot, A.4
-
260
-
-
0028131371
-
-
Verstegen-Haaksma, A. A.; Swarts, H. J.; Jansen, B. J. M.; de Groot, A. Tetrahedron 1994, 50, 10073.
-
(1994)
Tetrahedron
, vol.50
, pp. 10073
-
-
Verstegen-Haaksma, A.A.1
Swarts, H.J.2
Jansen, B.J.M.3
De Groot, A.4
-
261
-
-
33645380673
-
-
note
-
Direct attempts at generating 138 by conjugate addition of various metal enolates with different Michael acceptors were not successful, leading to a multistep sequence in which the angular nitrile was introduced by cyanide addition to an appropriately substituted enone: Girard M.; Studies directed towards the total synthesis of pentacyclic triterpenes, Ph.D. dissertation; Carleton University, Canada; 1985
-
-
-
-
262
-
-
33645420791
-
-
Girard, M.; ApSimon, J. W.; Huber, C. P. Can. J. Chem. 1987, 65, 191.
-
(1987)
Can. J. Chem.
, vol.65
, pp. 191
-
-
Girard, M.1
Apsimon, J.W.2
Huber, C.P.3
-
265
-
-
0028308321
-
-
Bailey, P. D.; Hollinshead, S. P.; Moore, M. H.; Morgan, K. M.; Smith, D. Y.; Vernon, J. M. Tetrahedron Lett. 1994, 35, 3585.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 3585
-
-
Bailey, P.D.1
Hollinshead, S.P.2
Moore, M.H.3
Morgan, K.M.4
Smith, D.Y.5
Vernon, J.M.6
-
266
-
-
0029082232
-
-
Mehmandoust, M.; Buisson, D.; Azerad, R. Tetrahedron Lett. 1995, 36, 6461.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 6461
-
-
Mehmandoust, M.1
Buisson, D.2
Azerad, R.3
-
271
-
-
33645387814
-
-
(a) Riobé, O.; Lamant, M.; Bussière, F. C. R. Hebd. Seances Acad. Sci. 1963, 256, 4026.
-
(1963)
C. R. Hebd. Seances Acad. Sci.
, vol.256
, pp. 4026
-
-
Riobé, O.1
Lamant, M.2
Bussière, F.3
-
273
-
-
0001479390
-
-
Marshall, J. A.; Karas, L. J.; Royce, D. R. Jr. J. Org. Chem. 1979, 44, 2994.
-
(1979)
J. Org. Chem.
, vol.44
, pp. 2994
-
-
Marshall, J.A.1
Karas, L.J.2
Royce Jr., D.R.3
-
274
-
-
0033543626
-
-
Shia, K.-S.; Jan, N.-W.; Zhu, J.-L.; Ly, T. W.; Liu, H.-J. Tetrahedron Lett. 1999, 40, 6753.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 6753
-
-
Shia, K.-S.1
Jan, N.-W.2
Zhu, J.-L.3
Ly, T.W.4
Liu, H.-J.5
-
276
-
-
0001964537
-
-
Arseniyadis, S.; Kyler, K. S.; Watt, D. S. Org. React. 1984, 31, 1.
-
(1984)
Org. React.
, vol.31
, pp. 1
-
-
Arseniyadis, S.1
Kyler, K.S.2
Watt, D.S.3
-
277
-
-
13844297054
-
-
Fleming, F. F.; Zhang, Z.; Wei, G.; Steward, O. W. Org. Lett. 2005, 7, 447.
-
(2005)
Org. Lett.
, vol.7
, pp. 447
-
-
Fleming, F.F.1
Zhang, Z.2
Wei, G.3
Steward, O.W.4
-
279
-
-
33645412439
-
-
note
-
3a,c,d
-
-
-
-
280
-
-
0001703411
-
-
(a) Fleming, F. F.; Pu, Y.; Tercek, F. J. Org. Chem. 1997, 62, 4883.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 4883
-
-
Fleming, F.F.1
Pu, Y.2
Tercek, F.3
-
281
-
-
0142042812
-
-
(b) For Grignard additions to five-membered oxonitriles, see: Kung, L.-R.; Tu, C.-H.; Shia, K.-S.; Liu, H.-J. Chem. Commun. 2003, 2490.
-
(2003)
Chem. Commun.
, pp. 2490
-
-
Kung, L.-R.1
Tu, C.-H.2
Shia, K.-S.3
Liu, H.-J.4
-
283
-
-
4243862792
-
-
(a) Ivanyuk, T. V.; Kadushkin, A. V.; Solov'eva, N. P.; Granik, V. V. Mendeleev Commun. 1993, 3, 160.
-
(1993)
Mendeleev Commun.
, vol.3
, pp. 160
-
-
Ivanyuk, T.V.1
Kadushkin, A.V.2
Solov'Eva, N.P.3
Granik, V.V.4
-
284
-
-
33645401593
-
-
(b) Strakov, A. Y.; Polis, O. P.; Sliede, Y. B.; Gundrinietce, E. Y. Izv. Akad. Nauk Latv. SSR, Ser. Khim. 1977, 337;
-
(1977)
Akad. Nauk Latv. SSR, Ser. Khim.
, vol.337
-
-
Strakov, A.Y.1
Polis, O.P.2
Sliede, Y.B.3
Izv, G.E.Y.4
-
285
-
-
33645406611
-
-
Chem. Abstr. 1977, 87, 151737.
-
(1977)
Chem. Abstr.
, vol.87
, pp. 151737
-
-
-
286
-
-
33645382940
-
-
(c) Akhrem, A. A.; Moiseenkov, A. M.; Strakov, A. Y.; Andaburskaya, M. B. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1973, 4, 811.
-
(1973)
Bull. Acad. Sci. USSR, Div. Chem. Sci.
, vol.4
, pp. 811
-
-
Akhrem, A.A.1
Moiseenkov, A.M.2
Strakov, A.Y.3
Andaburskaya, M.B.4
-
287
-
-
3242794728
-
-
(d) Strakov, A. Y.; Andaburskaya, M. B.; Moiseenkov, A. M. Izv. Akad. Nauk Latv. SSR, Ser. Khim. 1973, 836;
-
(1973)
Izv. Akad. Nauk Latv. SSR, Ser. Khim.
, pp. 836
-
-
Strakov, A.Y.1
Andaburskaya, M.B.2
Moiseenkov, A.M.3
-
288
-
-
33645419387
-
-
Chem. Abstr. 1973, 79, 31545.
-
(1973)
Chem. Abstr.
, vol.79
, pp. 31545
-
-
-
292
-
-
4644312993
-
-
(b) Tortajada, J.; Van Hemelryck, B.; Morizur, J.-P. Tetrahedron 1984, 40, 613.
-
(1984)
Tetrahedron
, vol.40
, pp. 613
-
-
Tortajada, J.1
Van Hemelryck, B.2
Morizur, J.-P.3
-
294
-
-
16044365485
-
-
(d) Tokuda, M.; Watanabe, Y.; Itoh, M. Bull. Chem. Soc. Jpn. 1978, 51, 905.
-
(1978)
Bull. Chem. Soc. Jpn.
, vol.51
, pp. 905
-
-
Tokuda, M.1
Watanabe, Y.2
Itoh, M.3
-
297
-
-
4644228499
-
-
Rüedi, G.; Oberli, M. A.; Hansen, H.-J. Tetrahedron Lett. 2004, 45, 7887.
-
(2004)
Tetrahedron Lett.
, vol.45
, pp. 7887
-
-
Rüedi, G.1
Oberli, M.A.2
Hansen, H.-J.3
-
299
-
-
0035910843
-
-
(a) Martínez, A. G.; Vilar, E. T.; Fraile, A. G.; de la Moya Cerero, S.; Maroto, B. L. Tetrahedron: Asymmetry 2001, 12, 189.
-
(2001)
Tetrahedron: Asymmetry
, vol.12
, pp. 189
-
-
Martínez, A.G.1
Vilar, E.T.2
Fraile, A.G.3
De La Moya Cerero, S.4
Maroto, B.L.5
-
300
-
-
33645420545
-
-
(b) Smith, E. M.; Shapiro, E. L.; Teutsch, G.; Weber, L.; Herzog, H. L.; McPhail, A. T.; Tschang, P.-S. W.; Meinwald, J. Tetrahedron Lett. 1974, 3519.
-
(1974)
Tetrahedron Lett.
, pp. 3519
-
-
Smith, E.M.1
Shapiro, E.L.2
Teutsch, G.3
Weber, L.4
Herzog, H.L.5
McPhail, A.T.6
Tschang, P.-S.W.7
Meinwald, J.8
-
303
-
-
84987298363
-
-
Hesse, M.; Milenkov, B.; Stojanova, D. S. Helv. Chim. Acta 1993, 76, 2303.
-
(1993)
Helv. Chim. Acta
, vol.76
, pp. 2303
-
-
Hesse, M.1
Milenkov, B.2
Stojanova, D.S.3
-
306
-
-
0030003497
-
-
Ivancev, W.; Ognyanov, V. I.; Hesse, M. Tetrahedron 1996, 57, 4363.
-
(1996)
Tetrahedron
, vol.57
, pp. 4363
-
-
Ivancev, W.1
Ognyanov, V.I.2
Hesse, M.3
-
308
-
-
37049086441
-
-
Cocker, W.; Grayson, D. H.; Shannon, P. V. R. J. Chem. Soc., Perkin Trans. 1 1995, 1153.
-
(1995)
J. Chem. Soc., Perkin Trans. 1
, pp. 1153
-
-
Cocker, W.1
Grayson, D.H.2
Shannon, P.V.R.3
-
310
-
-
0003468214
-
-
For related reactions with pyran-containing oxonitriles, see: (a) Seth, P. P.; Totah, N. I. Org. Lett. 1999, 1, 1411.
-
(1999)
Org. Lett.
, vol.1
, pp. 1411
-
-
Seth, P.P.1
Totah, N.I.2
-
312
-
-
0033583017
-
-
(c) Chen, D.; Wang, J.; Totah, N. I. J. Org. Chem. 1999, 64, 1776.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 1776
-
-
Chen, D.1
Wang, J.2
Totah, N.I.3
-
313
-
-
0033550224
-
-
(d) Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 8736
-
-
Hsung, R.P.1
Zificsak, C.A.2
Wei, L.-L.3
Zehnder, L.R.4
Park, F.5
Kim, M.6
Tran, T.-T.T.7
-
316
-
-
33645395143
-
-
Chem. Abstr. 1984, 101, 509891.
-
(1984)
Chem. Abstr.
, vol.101
, pp. 509891
-
-
-
317
-
-
0001123358
-
-
(a) Saito, I.; Shimozono, K.; Matsurura, T. J. Org. Chem. 1982, 47, 4356.
-
(1982)
J. Org. Chem.
, vol.47
, pp. 4356
-
-
Saito, I.1
Shimozono, K.2
Matsurura, T.3
-
321
-
-
1242336385
-
-
(c) Serebryakov, E. P.; Kulomzina-Pletneva, S. D.; Margaryan, A. K. Tetrahedron 1979, 35, 77.
-
(1979)
Tetrahedron
, vol.35
, pp. 77
-
-
Serebryakov, E.P.1
Kulomzina-Pletneva, S.D.2
Margaryan, A.K.3
-
322
-
-
0008492722
-
-
(a) Mallik, R.; Chatterjee, A. Indian J. Chem., Sect. B: Org. Chem. Ind. Med. Chem. 1993, 32, 811.
-
(1993)
Indian J. Chem., Sect. B: Org. Chem. Ind. Med. Chem.
, vol.32
, pp. 811
-
-
Mallik, R.1
Chatterjee, A.2
-
325
-
-
0001529462
-
-
(d) Banerjee, D. K.; Chatterjee, S.; Pillai, C. N.; Bhatt, M. V. J. Am. Chem. Soc. 1956, 78, 3769.
-
(1956)
J. Am. Chem. Soc.
, vol.78
, pp. 3769
-
-
Banerjee, D.K.1
Chatterjee, S.2
Pillai, C.N.3
Bhatt, M.V.4
-
327
-
-
0029980341
-
-
Cannella, R.; Clerici, F.; Gelmi, M. L.; Penso, M.; Pocar, D. J. Org. Chem. 1996, 61, 1854.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 1854
-
-
Cannella, R.1
Clerici, F.2
Gelmi, M.L.3
Penso, M.4
Pocar, D.5
-
328
-
-
84980284248
-
-
Plescia, S.; Aiello, E.; Daidone, G.; Sprio, V. J. Heterocycl. Chem. 1976, 13, 395.
-
(1976)
J. Heterocycl. Chem.
, vol.13
, pp. 395
-
-
Plescia, S.1
Aiello, E.2
Daidone, G.3
Sprio, V.4
-
329
-
-
0033600829
-
-
Zhu, J.-L.; Shia, K.-S.; Liu, H.-J. Tetrahedron Lett. 1999, 40, 7055.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 7055
-
-
Zhu, J.-L.1
Shia, K.-S.2
Liu, H.-J.3
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