-
1
-
-
77956215910
-
-
For a seminal review on Ficini [2 + 2] cycloaddition using ynamines, see
-
For a seminal review on Ficini [2 + 2] cycloaddition using ynamines, see
-
-
-
-
3
-
-
77956224179
-
-
For two other comprehensive reviews on ynamine chemistry, see
-
For two other comprehensive reviews on ynamine chemistry, see
-
-
-
-
4
-
-
0642263305
-
-
Kropf, H.,; Schaumann, E.; Georg Thieme Verlag: Stuttgart
-
Himbert, G. Methoden Der Organischen Chemie (Houben-Weyl); Kropf, H.,; Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1993; pp 3267 - 3443.
-
(1993)
Methoden der Organischen Chemie (Houben-Weyl)
, pp. 3267-3443
-
-
Himbert, G.1
Kropf, H.2
Schaumann, E.3
-
5
-
-
0035801916
-
-
Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575
-
(2001)
Tetrahedron
, vol.57
, pp. 7575
-
-
Zificsak, C.A.1
Mulder, J.A.2
Hsung, R.P.3
Rameshkumar, C.4
Wei, L.-L.5
-
6
-
-
77956215629
-
-
For a review on thermal [2 + 2] cycloaddition reactions, see
-
For a review on thermal [2 + 2] cycloaddition reactions, see
-
-
-
-
7
-
-
0002648396
-
-
Trost, B. M.; Fleming, I.; Pattenden, G., Eds.; Pergamon Press: New York
-
Baldwin, J. E. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Pattenden, G., Eds.; Pergamon Press: New York, 1991; Vol. 5, p 63.
-
(1991)
Comprehensive Organic Synthesis
, vol.5
, pp. 63
-
-
Baldwin, J.E.1
-
12
-
-
49349132056
-
-
Ficini, J.; Falou, S.; d'Angelo, J. Tetrahedron Lett. 1977, 18, 1931.
-
(1977)
Tetrahedron Lett.
, vol.18
, pp. 1931
-
-
Ficini, J.1
Falou, S.2
Dangelo, J.3
-
13
-
-
77956216258
-
-
For cycloadditions to quinone, see
-
For cycloadditions to quinone, see
-
-
-
-
15
-
-
77956217997
-
-
For related examples that were contemporary, see
-
For related examples that were contemporary, see
-
-
-
-
19
-
-
77956194670
-
-
For Ficini s later work, see
-
For Ficini s later work, see
-
-
-
-
20
-
-
0020677879
-
-
Ficini, J.; Guingant, A.; d'Angelo, J.; Stork, G. Tetrahedron Lett. 1983, 24, 907
-
(1983)
Tetrahedron Lett.
, vol.24
, pp. 907
-
-
Ficini, J.1
Guingant, A.2
D'angelo, J.3
Stork, G.4
-
21
-
-
0141826093
-
-
Ficini, J.; Krief, A.; Guingant, A.; Desmaele, D. Tetrahedron Lett. 1981, 22, 725
-
(1981)
Tetrahedron Lett.
, vol.22
, pp. 725
-
-
Ficini, J.1
Krief, A.2
Guingant, A.3
Desmaele, D.4
-
22
-
-
77956223665
-
-
For comprehensive reviews on chemistry of ynamides, see
-
For comprehensive reviews on chemistry of ynamides, see
-
-
-
-
23
-
-
77956213455
-
-
ASAP
-
DeKorver, K. A.; Li, H.; Lohse, A. G.; Hayashi, R.; Shi, Z.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2010, 110, ASAP.
-
(2010)
Chem. Rev.
, vol.110
-
-
Dekorver, K.A.1
Li, H.2
Lohse, A.G.3
Hayashi, R.4
Shi, Z.5
Zhang, Y.6
Hsung, R.P.7
-
24
-
-
77950513362
-
-
Evano, G.; Coste, A.; Jouvin, K. Angew. Chem., Int. Ed. 2010, 49, 2840
-
(2010)
Angew. Chem., Int. Ed.
, vol.49
, pp. 2840
-
-
Evano, G.1
Coste, A.2
Jouvin, K.3
-
25
-
-
77956214284
-
-
For recent examples, see
-
For recent examples, see
-
-
-
-
26
-
-
77954608063
-
-
Li, H.; Antoline, J. E.; Yang, J.-H.; Al-Rashid, Z. F.; Hsung, R. P. New J. Chem. 2010, 34, 1309
-
(2010)
New J. Chem.
, vol.34
, pp. 1309
-
-
Li, H.1
Antoline, J.E.2
Yang, J.-H.3
Al-Rashid, Z.F.4
Hsung, R.P.5
-
27
-
-
77953593987
-
-
Kramer, S.; Madsen, J. L. H.; Rottländer, M.; Skrydstrup, T. Org. Lett. 2010, 12, 2758
-
(2010)
Org. Lett.
, vol.12
, pp. 2758
-
-
Kramer, S.1
Madsen, J.L.H.2
Rottländer, M.3
Skrydstrup, T.4
-
28
-
-
77953016274
-
-
Banerjee, B.; Litvinov, D. N.; Kang, J.; Bettale, J. D.; Castle, S. L. Org. Lett. 2010, 12, 2650
-
(2010)
Org. Lett.
, vol.12
, pp. 2650
-
-
Banerjee, B.1
Litvinov, D.N.2
Kang, J.3
Bettale, J.D.4
Castle, S.L.5
-
29
-
-
77953013396
-
-
Gourdet, B.; Rudkin, M. E.; Lam, H. W. Org. Lett. 2010, 12, 2554
-
(2010)
Org. Lett.
, vol.12
, pp. 2554
-
-
Gourdet, B.1
Rudkin, M.E.2
Lam, H.W.3
-
31
-
-
77951185847
-
-
DeKorver, K. A.; Hsung, R. P.; Lohse, A. G.; Zhang, Y. Org. Lett. 2010, 12, 1840
-
(2010)
Org. Lett.
, vol.12
, pp. 1840
-
-
Dekorver, K.A.1
Hsung, R.P.2
Lohse, A.G.3
Zhang, Y.4
-
32
-
-
75749107815
-
-
Burley, G. A.; Davies, D. L.; Griffith, G. A.; Lee, M.; Singh, K. J. Org. Chem. 2010, 75, 980
-
(2010)
J. Org. Chem.
, vol.75
, pp. 980
-
-
Burley, G.A.1
Davies, D.L.2
Griffith, G.A.3
Lee, M.4
Singh, K.5
-
33
-
-
75349095927
-
-
Yamasaki, R.; Terashima, N.; Sotome, I.; Komagawa, S.; Saito, S. J. Org. Chem. 2010, 75, 480
-
(2010)
J. Org. Chem.
, vol.75
, pp. 480
-
-
Yamasaki, R.1
Terashima, N.2
Sotome, I.3
Komagawa, S.4
Saito, S.5
-
34
-
-
24044461397
-
-
Riddell, N.; Villeneuve, K.; Tam, W. Org. Lett. 2005, 7, 3681
-
(2005)
Org. Lett.
, vol.7
, pp. 3681
-
-
Riddell, N.1
Villeneuve, K.2
Tam, W.3
-
35
-
-
68049129443
-
-
Cockburn, N.; Karimi, E.; Tam, W. J. Org. Chem. 2009, 74, 5762
-
(2009)
J. Org. Chem.
, vol.74
, pp. 5762
-
-
Cockburn, N.1
Karimi, E.2
Tam, W.3
-
36
-
-
33645324752
-
-
Kohnen, A. L.; Mak, X. Y.; Lam, T. Y.; Dunetz, J. R.; Danheiser, R. L. Tetrahedron 2006, 62, 3815
-
(2006)
Tetrahedron
, vol.62
, pp. 3815
-
-
Kohnen, A.L.1
Mak, X.Y.2
Lam, T.Y.3
Dunetz, J.R.4
Danheiser, R.L.5
-
37
-
-
2442478471
-
-
Marion, F.; Coulomb, J.; Courillon, C.; Fensterbank, L.; Malacria, M. Org. Lett. 2004, 6, 1509
-
(2004)
Org. Lett.
, vol.6
, pp. 1509
-
-
Marion, F.1
Coulomb, J.2
Courillon, C.3
Fensterbank, L.4
Malacria, M.5
-
38
-
-
33645298511
-
-
Marion, F.; Coulomb, J.; Servais, A.; Courillon, C.; Fensterbank, L.; Malacria, M. Tetrahedron 2006, 62, 3856
-
(2006)
Tetrahedron
, vol.62
, pp. 3856
-
-
Marion, F.1
Coulomb, J.2
Servais, A.3
Courillon, C.4
Fensterbank, L.5
Malacria, M.6
-
40
-
-
33750194180
-
-
Couty, S.; Meyer, C.; Cossy, J. Angew. Chem., Int. Ed. 2006, 45, 6726
-
(2006)
Angew. Chem., Int. Ed.
, vol.45
, pp. 6726
-
-
Couty, S.1
Meyer, C.2
Cossy, J.3
-
41
-
-
58949090317
-
-
Couty, S.; Meyer, C.; Cossy, J. Tetrahedron 2009, 65, 1809
-
(2009)
Tetrahedron
, vol.65
, pp. 1809
-
-
Couty, S.1
Meyer, C.2
Cossy, J.3
-
42
-
-
84855625629
-
-
2, see
-
2, see
-
-
-
-
43
-
-
2942687050
-
-
Sweis, R. F.; Schramm, M. P.; Kozmin, S. A. J. Am. Chem. Soc. 2004, 126, 7442
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 7442
-
-
Sweis, R.F.1
Schramm, M.P.2
Kozmin, S.A.3
-
44
-
-
0141630352
-
-
Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P.; Coverdale, H. A.; Frederick, M. O.; Shen, L.; Zificsak, C. A. Org. Lett. 2003, 5, 1547.
-
(2003)
Org. Lett.
, vol.5
, pp. 1547
-
-
Mulder, J.A.1
Kurtz, K.C.M.2
Hsung, R.P.3
Coverdale, H.A.4
Frederick, M.O.5
Shen, L.6
Zificsak, C.A.7
-
45
-
-
77956206339
-
-
note
-
2 in general because of the overall stability difference between the respective conjugate bases [as one referee kindly pointed out], sulfonyl-substituted ynamides [or enamides] are more reactive and less stable than simple amide or urethane-substituted ynamides [or enamide]. The nitrogen lone pair in the former is more delocalized into the alkyne [or alkene motif] and more into the carbonyl group in the latter. Likewise, but in a reverse sense, for iminium ion chemistry, sulfonyl-substituted iminium species are more stable and less reactive than straight N-acyl iminium ions because the nitrogen lone pair in the former is more involved in the π-donation to the carbocation. See
-
-
-
-
46
-
-
2942574530
-
-
Royer, J.; Bonin, M.; Micouin, L. Chem. Rev. 2004, 104, 2311
-
(2004)
Chem. Rev.
, vol.104
, pp. 2311
-
-
Royer, J.1
Bonin, M.2
Micouin, L.3
-
47
-
-
31544442421
-
-
Kurtz, K. C. M.; Hsung, R. P.; Zhang, Y. Org. Lett. 2006, 8, 231
-
(2006)
Org. Lett.
, vol.8
, pp. 231
-
-
Kurtz, K.C.M.1
Hsung, R.P.2
Zhang, Y.3
-
48
-
-
77956207383
-
-
note
-
For α-halogenations of ynamides observed using Pd(0) and Rh(I), see
-
-
-
-
49
-
-
3142699919
-
-
Tracey, M. R.; Zhang, Y.; Frederick, M. O.; Mulder, J. A.; Hsung, R. P. Org. Lett. 2004, 6, 2209
-
(2004)
Org. Lett.
, vol.6
, pp. 2209
-
-
Tracey, M.R.1
Zhang, Y.2
Frederick, M.O.3
Mulder, J.A.4
Hsung, R.P.5
-
50
-
-
34250867364
-
-
Oppenheimer, J.; Johnson, W. L.; Tracey, M. R.; Hsung, R. P.; Yao, P.-Y.; Liu, R.; Zhao, K. Org. Lett. 2007, 9, 2361
-
(2007)
Org. Lett.
, vol.9
, pp. 2361
-
-
Oppenheimer, J.1
Johnson, W.L.2
Tracey, M.R.3
Hsung, R.P.4
Yao, P.-Y.5
Liu, R.6
Zhao, K.7
-
51
-
-
77956210127
-
-
See Supporting Information
-
See Supporting Information.
-
-
-
-
54
-
-
33947482868
-
-
Corey, E. J.; Bass, J. D.; Le Mahisu, R.; Mitra, R. B. J. Am. Chem. Soc. 1964, 86, 5570
-
(1964)
J. Am. Chem. Soc.
, vol.86
, pp. 5570
-
-
Corey, E.J.1
Bass, J.D.2
Le Mahisu, R.3
Mitra, R.B.4
-
55
-
-
77956222619
-
-
note
-
Conjugation appears to be a key, as cyclohexenyl methyl ketone did not give i when reacted with ynamide 12. On the other hand, cyclohexenyl nitrile gave a completely different product pyrimidine iii, thereby suggesting a cyclotrimerization process. Regiochemistry of iii was assigned using NOE [see Supporting Information ].
-
-
-
-
56
-
-
33751499216
-
-
Mikami, K.; Terada, M.; Nakai, T. J. Org. Chem. 1991, 56, 5456
-
(1991)
J. Org. Chem.
, vol.56
, pp. 5456
-
-
Mikami, K.1
Terada, M.2
Nakai, T.3
-
57
-
-
77956209461
-
-
note
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Keto-imide 31 could be further hydrolyzed to 30-syn and 30-anti in 1:1 ratio using the same conditions.
-
-
-
-
59
-
-
1542783486
-
-
Ficini, J.; Desmaele, D.; Touzin, A.-M. Tetrahedron Lett. 1983, 24, 1025
-
(1983)
Tetrahedron Lett.
, vol.24
, pp. 1025
-
-
Ficini, J.1
Desmaele, D.2
Touzin, A.-M.3
-
60
-
-
49549130549
-
-
Ficini, J.; Eman, A.; Touzin, A.-M. Tetrahedron Lett. 1976, 17, 679
-
(1976)
Tetrahedron Lett.
, vol.17
, pp. 679
-
-
Ficini, J.1
Eman, A.2
Touzin, A.-M.3
-
61
-
-
0007642384
-
-
Ficini, J.; d'Angelo, J.; Noiré, J. J. Am. Chem. Soc. 1974, 96, 1213
-
(1974)
J. Am. Chem. Soc.
, vol.96
, pp. 1213
-
-
Ficini, J.1
D'angelo, J.2
Noiré, J.3
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