-
1
-
-
84869271067
-
-
Nitrogen Heterocycles: (a) Bäckvall, J. E.; Nyström, J. E. J. Chem. Soc., Chem. Commun. 1981, 5, 9-61.
-
Nitrogen Heterocycles: (a) Bäckvall, J. E.; Nyström, J. E. J. Chem. Soc., Chem. Commun. 1981, 5, 9-61.
-
-
-
-
4
-
-
0343899334
-
-
Oxygen heterocycles
-
(d) Riesinger, S. W.; Lofstedt, J.; Pettersson-Fasth, H.; Bäckvall, J.-E. Eur. J. Org. Chem, 1999, 3277-3280. Oxygen heterocycles:
-
(1999)
Eur. J. Org. Chem
, pp. 3277-3280
-
-
Riesinger, S.W.1
Lofstedt, J.2
Pettersson-Fasth, H.3
Bäckvall, J.-E.4
-
6
-
-
0029043318
-
-
(f) Koroleva, E. B.; Bäckvall, J.-E.; Andersson, P. G. Tetrahedron Lett. 1995, 36, 5397-5400.
-
(1995)
Tetrahedron Lett
, vol.36
, pp. 5397-5400
-
-
Koroleva, E.B.1
Bäckvall, J.-E.2
Andersson, P.G.3
-
7
-
-
0029923002
-
-
(g) Nilsson, Y. I. M.; Aranyos, A.; Andersson, P. G.; Bäckvall, J.-E.; Parrain, J.-L.; Ploteau, C.; Quintard, J.-P. J. Org. Chem. 1996, 61, 1825-1829.
-
(1996)
J. Org. Chem
, vol.61
, pp. 1825-1829
-
-
Nilsson, Y.I.M.1
Aranyos, A.2
Andersson, P.G.3
Bäckvall, J.-E.4
Parrain, J.-L.5
Ploteau, C.6
Quintard, J.-P.7
-
8
-
-
0032485423
-
-
(h) Itami, K.; Palmgren, A.; Bäckvall, J.-E. Tetrahedron Lett. 1998, 39, 1223-1226.
-
(1998)
Tetrahedron Lett
, vol.39
, pp. 1223-1226
-
-
Itami, K.1
Palmgren, A.2
Bäckvall, J.-E.3
-
9
-
-
2142698607
-
-
(i) Verboom, R. C.; Persson, B. A.; Bäckvall, J.-E. J. Org. Chem. 2004, 69, 3102-3111.
-
(2004)
J. Org. Chem
, vol.69
, pp. 3102-3111
-
-
Verboom, R.C.1
Persson, B.A.2
Bäckvall, J.-E.3
-
10
-
-
33748978228
-
-
Middleton, M. D.; Peppers, B. P.; Diver, S. T. Tetrahedron 2006, 62, 10528-10540.
-
(2006)
Tetrahedron
, vol.62
, pp. 10528-10540
-
-
Middleton, M.D.1
Peppers, B.P.2
Diver, S.T.3
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13
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13244289965
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In this case, only E-4A was detected. In the cross metathesis step with simple alkenes, longer periods of heating give primarily the E-isomer: (a) Giessert, A. J.; Diver, S. T. J. Org. Chem. 2005, 70, 1046-1049.
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In this case, only E-4A was detected. In the cross metathesis step with simple alkenes, longer periods of heating give primarily the E-isomer: (a) Giessert, A. J.; Diver, S. T. J. Org. Chem. 2005, 70, 1046-1049.
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14
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33845448137
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-
(b) Clark, D. A.; Kulkarni, A. A.; Kalbarczyk, K.; Schertzer, B.; Diver, S. T. J. Am. Chem. Soc. 2006, 128, 15632-15636.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 15632-15636
-
-
Clark, D.A.1
Kulkarni, A.A.2
Kalbarczyk, K.3
Schertzer, B.4
Diver, S.T.5
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15
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64249104874
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Similar studies were conducted with pure, E-4B: 4 equiv TFA promoted the cyclization 100% conversion, 73% isolated, However, in the one-pot reaction, 4 equiv of TFA did not result in full conversion of the intermediate 1,3-diene. Since excess alkene was still present, higher amounts of acid were needed, see ref 8
-
Similar studies were conducted with pure, E-4B: 4 equiv TFA promoted the cyclization (100% conversion, 73% isolated). However, in the one-pot reaction, 4 equiv of TFA did not result in full conversion of the intermediate 1,3-diene. Since excess alkene was still present, higher amounts of acid were needed, see ref 8.
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17
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33749000858
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(b) Rosenfeld, D. C.; Shekhar, S.; Takemiya, A.; Utsunomiya, M.; Hartwig, J. F. Org. Lett. 2006, 8, 4179-4182.
-
(2006)
Org. Lett
, vol.8
, pp. 4179-4182
-
-
Rosenfeld, D.C.1
Shekhar, S.2
Takemiya, A.3
Utsunomiya, M.4
Hartwig, J.F.5
-
18
-
-
33749036284
-
-
Li, Z.; Zhans, J.; Brouwer, C.; Yang, C.-G.; Reich Nicholas, W.: He, C. Org. Lett. 2006, 8, 4175-4178.
-
(2006)
Org. Lett
, vol.8
, pp. 4175-4178
-
-
Li, Z.1
Zhans, J.2
Brouwer, C.3
Yang, C.-G.4
Reich Nicholas, W.5
He, C.6
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19
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64249096178
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Interestingly, the He study (ref 7) reported intermolecular 1,2-hydroamination of unactivated alkenes. In the present case, it is likely that some loss of material is due to addition reactions to remaining 1-hexene.
-
Interestingly, the He study (ref 7) reported intermolecular 1,2-hydroamination of unactivated alkenes. In the present case, it is likely that some loss of material is due to addition reactions to remaining 1-hexene.
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20
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64249103075
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See the Supporting Information
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See the Supporting Information.
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21
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0034815578
-
-
(a) Hedley, S. J.; Moran, W. J.; Prenzel, A. H. G. P.; Price, D. A.; Harrity, J. P. A. Synlett 2001, 10, 1596-1598.
-
(2001)
Synlett
, vol.10
, pp. 1596-1598
-
-
Hedley, S.J.1
Moran, W.J.2
Prenzel, A.H.G.P.3
Price, D.A.4
Harrity, J.P.A.5
-
22
-
-
1642288601
-
-
(b) Hersh, W. H.; Xu, P.; Simpson, C. K.; Grob, J.; Bickford, B.; Hamdani, M. S.; Wood, T.; Rheingold, A. L. J. Org. Chem. 2004, 69, 2153-2163.
-
(2004)
J. Org. Chem
, vol.69
, pp. 2153-2163
-
-
Hersh, W.H.1
Xu, P.2
Simpson, C.K.3
Grob, J.4
Bickford, B.5
Hamdani, M.S.6
Wood, T.7
Rheingold, A.L.8
-
23
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0023779454
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1,3 strain was invoked in N-acyl piperidinone to explain diastereoselection during conjugate addition reactions: (a) Brown, J. D.; Foley, M. A.; Comins, D. L J. Org 1988, 110, 7445-7447. For similar reasons, the N-tosyl group in a piperidine ring system causes the 2-substituent to occupy an axial position.
-
1,3 strain was invoked in N-acyl piperidinone to explain diastereoselection during conjugate addition reactions: (a) Brown, J. D.; Foley, M. A.; Comins, D. L J. Org 1988, 110, 7445-7447. For similar reasons, the N-tosyl group in a piperidine ring system causes the 2-substituent to occupy an axial position.
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-
-
-
24
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0002240151
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-
and ref 10. See: b
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See: (b) Craig, D. L.; McCague, R.; Potter, G.; Williams, M. R. V. Synlett 1998, 55-57, and ref 10.
-
(1998)
Synlett
, pp. 55-57
-
-
Craig, D.L.1
McCague, R.2
Potter, G.3
Williams, M.R.V.4
-
26
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-
0034051322
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-
Other ring-rearrangements: Piperidine: a
-
Piperidine: (a) Voigtmann, U.; Blechert, S. Synthesis 2000, 893-898. Other ring-rearrangements:
-
(2000)
Synthesis
, pp. 893-898
-
-
Voigtmann, U.1
Blechert, S.2
-
27
-
-
0012748919
-
-
(b) Randl, S.; Lucas, N.; Connon, S. J.; Blechert, S. Adv. Synth. Cat. 2002, 344, 631-633.
-
(2002)
Adv. Synth. Cat
, vol.344
, pp. 631-633
-
-
Randl, S.1
Lucas, N.2
Connon, S.J.3
Blechert, S.4
-
29
-
-
33745053040
-
-
(d) Boehrsch, V.; Neidhoefer, J.; Blechert, S. Angew. Chem., Int. Ed. 2006, 45, 1302-1305.
-
(2006)
Angew. Chem., Int. Ed
, vol.45
, pp. 1302-1305
-
-
Boehrsch, V.1
Neidhoefer, J.2
Blechert, S.3
-
31
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64249085129
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In this case, fewer equivalents of TFA were found to promote the cyclization. Carbene 1 also promoted this metathesis.
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In this case, fewer equivalents of TFA were found to promote the cyclization. Carbene 1 also promoted this metathesis.
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32
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34147157753
-
-
Galan, B. R.; Kalbarczyk, K. P.; Szczepankiewicz, S.; Keister, J. B.; Diver, S. T. Org. Lett. 2007, 9, 1203-1206.
-
(2007)
Org. Lett
, vol.9
, pp. 1203-1206
-
-
Galan, B.R.1
Kalbarczyk, K.P.2
Szczepankiewicz, S.3
Keister, J.B.4
Diver, S.T.5
-
33
-
-
60949091784
-
-
Use of methylene cyclobutane in enyne metathesis: Clark, D. C.; Karnofel, W.; Basile, B.; Diver, S. T. Org. Lett. 2008, 10, 4927-4929.
-
Use of methylene cyclobutane in enyne metathesis: Clark, D. C.; Karnofel, W.; Basile, B.; Diver, S. T. Org. Lett. 2008, 10, 4927-4929.
-
-
-
-
34
-
-
34247487884
-
-
(a) Stewart, I. C.; Ung, T.; Pletnev, A. A.; Berlin, J. M.; Grubbs, R. H.; Schrodi, Y. Org. Lett. 2007, 9, 1589-1592.
-
(2007)
Org. Lett
, vol.9
, pp. 1589-1592
-
-
Stewart, I.C.1
Ung, T.2
Pletnev, A.A.3
Berlin, J.M.4
Grubbs, R.H.5
Schrodi, Y.6
-
35
-
-
38949095222
-
-
(b) Stewart, I. C.; Douglas, C. J.; Grubbs, R. H. Org. Lett. 2008, 10, 441-444.
-
(2008)
Org. Lett
, vol.10
, pp. 441-444
-
-
Stewart, I.C.1
Douglas, C.J.2
Grubbs, R.H.3
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