-
4
-
-
84890577313
-
-
Evans, P. A, Ed, Wiley-VCH: Weinheim, Germany
-
(d) Doyle, M. P. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, Germany, 2005; pp 341-355.
-
(2005)
Modern Rhodium-Catalyzed Organic Reactions
, pp. 341-355
-
-
Doyle, M.P.1
-
5
-
-
84890769366
-
-
Evans, P. A, Ed, Wiley-VCH: Weinheim, Germany
-
(e) Taber, D. F.; Joshi, P. V. In Modem RhodiumCatalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, Germany, 2005; pp 357-377.
-
(2005)
Modem RhodiumCatalyzed Organic Reactions
, pp. 357-377
-
-
Taber, D.F.1
Joshi, P.V.2
-
7
-
-
0037668345
-
-
For recent examples, see: a
-
For recent examples, see: (a) Kurosawa, W.; Kan, T.; Fukuyama, T. J. Am. Chem. Soc. 2003, 125, 8112-8113.
-
(2003)
J. Am. Chem. Soc
, vol.125
, pp. 8112-8113
-
-
Kurosawa, W.1
Kan, T.2
Fukuyama, T.3
-
9
-
-
17044429442
-
-
(c) Davies, H. M. L.; Walji, A. M. Angew. Chem., Int. Ed. 2005, 44, 1733-1735.
-
(2005)
Angew. Chem., Int. Ed
, vol.44
, pp. 1733-1735
-
-
Davies, H.M.L.1
Walji, A.M.2
-
11
-
-
32244441287
-
-
(e) Reisman, S. E.; Ready, J. M.; Hasuoka, A.; Smith, C. J.; Wood, J. L. J. Am. Chem. Soc. 2006, 128, 1448-1449.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 1448-1449
-
-
Reisman, S.E.1
Ready, J.M.2
Hasuoka, A.3
Smith, C.J.4
Wood, J.L.5
-
12
-
-
33644544051
-
-
(f) Davies, H. M. L.; Dai, X.; Long, M. S. J. Am. Chem. Soc. 2006, 128, 2485-2490.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 2485-2490
-
-
Davies, H.M.L.1
Dai, X.2
Long, M.S.3
-
13
-
-
33748480130
-
-
(g) Tambar, U. K.; Ebner, D. C.; Stoltz, B. M. J. Am. Chem. Soc. 2006, 128, 11752-11753.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 11752-11753
-
-
Tambar, U.K.1
Ebner, D.C.2
Stoltz, B.M.3
-
15
-
-
0025073109
-
-
(b) Lee, E.; Jung, K. W.; Kim, Y. S. Tetrahedron Lett. 1990, 31, 1023-1026.
-
(1990)
Tetrahedron Lett
, vol.31
, pp. 1023-1026
-
-
Lee, E.1
Jung, K.W.2
Kim, Y.S.3
-
16
-
-
0000234509
-
-
(c) Doyle, M. P.; Westrum, L. J.; Wolthuis, W. N. E.; See, M. M.; Boone, W. P.; Bagheri, V.; Pearson, M. M. J. Am. Chem. Soc. 1993, 115, 958-964.
-
(1993)
J. Am. Chem. Soc
, vol.115
, pp. 958-964
-
-
Doyle, M.P.1
Westrum, L.J.2
Wolthuis, W.N.E.3
See, M.M.4
Boone, W.P.5
Bagheri, V.6
Pearson, M.M.7
-
17
-
-
33748811198
-
-
(d) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. 1994, 33, 1797-1815.
-
(1994)
Angew. Chem., Int. Ed
, vol.33
, pp. 1797-1815
-
-
Padwa, A.1
Austin, D.J.2
-
20
-
-
0034742992
-
-
(b) Aburel, P. S.; Romming, C.; Undheim, K. J. Chem. Soc., Perkin Trans. 1 2001, 1024-1029.
-
(2001)
J. Chem. Soc., Perkin Trans. 1
, pp. 1024-1029
-
-
Aburel, P.S.1
Romming, C.2
Undheim, K.3
-
21
-
-
32744474936
-
-
Lee, E.; Choi, I.; Song, S. Y. J. Chem. Soc., Chem. Commun. 1995, 321-322.
-
(1995)
J. Chem. Soc., Chem. Commun
, pp. 321-322
-
-
Lee, E.1
Choi, I.2
Song, S.Y.3
-
23
-
-
0029833299
-
-
(b) Doyle, M. P.; Dyatkin, A. V.; Ene, D. G. J. Am. Chem. Soc. 1996, 118, 8837-8846.
-
(1996)
J. Am. Chem. Soc
, vol.118
, pp. 8837-8846
-
-
Doyle, M.P.1
Dyatkin, A.V.2
Ene, D.G.3
-
24
-
-
0034835815
-
-
(a) Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935-6936.
-
(2001)
J. Am. Chem. Soc
, vol.123
, pp. 6935-6936
-
-
Espino, C.G.1
Wehn, P.M.2
Chow, J.3
Du Bois, J.4
-
25
-
-
0345791433
-
-
(b) Wehn, P. M.; Lee, J.; Du Bois, J. Org. Lett. 2003, 5, 4823-4826.
-
(2003)
Org. Lett
, vol.5
, pp. 4823-4826
-
-
Wehn, P.M.1
Lee, J.2
Du Bois, J.3
-
26
-
-
0035793265
-
-
(a) Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed. 2001, 40, 598-600.
-
(2001)
Angew. Chem., Int. Ed
, vol.40
, pp. 598-600
-
-
Espino, C.G.1
Du Bois, J.2
-
27
-
-
33646438818
-
-
(b) Lee, M.; Mulcahy, J. V.; Espino, C. G.; Du Bois, J. Org. Lett. 2006, 8, 1073-1076.
-
(2006)
Org. Lett
, vol.8
, pp. 1073-1076
-
-
Lee, M.1
Mulcahy, J.V.2
Espino, C.G.3
Du Bois, J.4
-
30
-
-
37049070843
-
-
Use of iodonium ylides as carbene precursors was originally advanced by Varvoglis and Moriarty, see: a
-
Use of iodonium ylides as carbene precursors was originally advanced by Varvoglis and Moriarty, see: (a) Hatjiarapoglou, L.; Varvoglis, A.; Alcock, N. W.; Pike, G. A. J. Chem. Soc., Perkin Trans. 1 1988, 2839-2846.
-
(1988)
J. Chem. Soc., Perkin Trans. 1
, pp. 2839-2846
-
-
Hatjiarapoglou, L.1
Varvoglis, A.2
Alcock, N.W.3
Pike, G.A.4
-
31
-
-
0001519750
-
-
For an excellent review on this subject, see
-
(b) Moriarty, R. M.; Prakash, O.; Vaid, R. K.; Zhao, L. J. Am. Chem. Soc. 1989, 111, 6443-6444. For an excellent review on this subject, see:
-
(1989)
J. Am. Chem. Soc
, vol.111
, pp. 6443-6444
-
-
Moriarty, R.M.1
Prakash, O.2
Vaid, R.K.3
Zhao, L.4
-
33
-
-
0034794306
-
-
For leading references, see: a
-
For leading references, see: (a) Dauban, P.; Saniere, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707-7708.
-
(2001)
J. Am. Chem. Soc
, vol.123
, pp. 7707-7708
-
-
Dauban, P.1
Saniere, L.2
Tarrade, A.3
Dodd, R.H.4
-
36
-
-
84890760012
-
-
Evans, P. A, Ed, Wiley-VCH: Weinheim, Germany
-
Espino, C. G.; Du Bois, J. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, Germany, 2005; pp 379-416.
-
(2005)
Modern Rhodium-Catalyzed Organic Reactions
, pp. 379-416
-
-
Espino, C.G.1
Du Bois, J.2
-
37
-
-
3643073215
-
-
Thermal reactions of diazosulfonates to generate alkene products have been reported, see
-
Thermal reactions of diazosulfonates to generate alkene products have been reported, see: Berkessel, A.; Voges, M. Chem. Ber. 1989, 122, 1147-1151.
-
(1989)
Chem. Ber
, vol.122
, pp. 1147-1151
-
-
Berkessel, A.1
Voges, M.2
-
38
-
-
0016725064
-
-
Sulfonyl chloride 2 was prepared following a modification of a procedure outlined by:, See the Supporting Information for details
-
Sulfonyl chloride 2 was prepared following a modification of a procedure outlined by: Oliver, J. E.; DeMilo, A. B. Synthesis 1975, 321-322. See the Supporting Information for details.
-
(1975)
Synthesis
, pp. 321-322
-
-
Oliver, J.E.1
DeMilo, A.B.2
-
39
-
-
84858345635
-
-
3N were considerably less effective.
-
3N were considerably less effective.
-
-
-
-
40
-
-
35548948134
-
-
Use of p-acetamidobenzenesulfonyl azide gave poor yield of the diazo compound and, instead, a significant amount of the alcohol, ROH, was generated
-
Use of p-acetamidobenzenesulfonyl azide gave poor yield of the diazo compound and, instead, a significant amount of the alcohol, ROH, was generated.
-
-
-
-
41
-
-
84858360757
-
-
Purified diazosulfonate derivatives are generally stable for weeks if stored at -20 °C In two cases (entries 2 and 4), decomposition was observed when these materials were left to stand overnight at 23 °C
-
Purified diazosulfonate derivatives are generally stable for weeks if stored at -20 °C In two cases (entries 2 and 4), decomposition was observed when these materials were left to stand overnight at 23 °C
-
-
-
-
42
-
-
84858356143
-
-
The addition of powdered 3 Åmolecular sieves was found to improve sultone yields in a few instances, see the Supporting Information for details.
-
The addition of powdered 3 Åmolecular sieves was found to improve sultone yields in a few instances, see the Supporting Information for details.
-
-
-
-
43
-
-
35548986330
-
-
Other Rh catalysts examined included Rh2(oct)4, Rh2(OPiV)4, Rh2(O2CCPh 3)4, Rh2(O2CCF3) 4, Rh2(NHCOCF3)4, and Rh 2(cap)4
-
4.
-
-
-
-
44
-
-
35548986772
-
-
In entry 4, the five-membered-ring product formed through benzylic C-H insertion was also obtained (42% yield).
-
In entry 4, the five-membered-ring product formed through benzylic C-H insertion was also obtained (42% yield).
-
-
-
-
45
-
-
0042803335
-
-
For select examples of transannular C-H insertions with diazoketones, see: a
-
For select examples of transannular C-H insertions with diazoketones, see: (a) Ghatak, U. R.; Chakrabarty, S. J. Am. Chem. Soc. 1972, 94, 4756-4758.
-
(1972)
J. Am. Chem. Soc
, vol.94
, pp. 4756-4758
-
-
Ghatak, U.R.1
Chakrabarty, S.2
-
47
-
-
37049075893
-
-
(c) West, F. G.; Eberlein, T. H.; Tester, R. W. J. Chem. Soc., Perkin Trans. 1 1993, 2857-2859.
-
(1993)
J. Chem. Soc., Perkin Trans. 1
, pp. 2857-2859
-
-
West, F.G.1
Eberlein, T.H.2
Tester, R.W.3
-
48
-
-
0032694765
-
-
(d) White, J. D.; Hrnciar, P.; Stappenbeck, F. J. Org. Chem. 1999, 64, 7871-7884.
-
(1999)
J. Org. Chem
, vol.64
, pp. 7871-7884
-
-
White, J.D.1
Hrnciar, P.2
Stappenbeck, F.3
-
49
-
-
0035954896
-
-
(e) Wardrop, D. J.; Velter, A. I.; Forslund, R. E. Org. Lett. 2001, 3, 2261-2264.
-
(2001)
Org. Lett
, vol.3
, pp. 2261-2264
-
-
Wardrop, D.J.1
Velter, A.I.2
Forslund, R.E.3
-
50
-
-
0343163312
-
-
A typical y-sultone C-S-O bond angle is ≤98°, see: (a) Billodeaux, D. R.; Owens, C. V.; Sayes, C. M.; Soper, S. A.; Fronczek, F. R. Acta Cryst. 1999, C55, 2126-2129.
-
A typical y-sultone C-S-O bond angle is ≤98°, see: (a) Billodeaux, D. R.; Owens, C. V.; Sayes, C. M.; Soper, S. A.; Fronczek, F. R. Acta Cryst. 1999, C55, 2126-2129.
-
-
-
-
51
-
-
0008631913
-
-
(b) Muir, K. W.; Rodger, C. S.; Morris, D. G.; Ryder, K. S. Acta Crysr. 1998, C54, 1546-1548.
-
(1998)
Acta Crysr
, vol.C54
, pp. 1546-1548
-
-
Muir, K.W.1
Rodger, C.S.2
Morris, D.G.3
Ryder, K.S.4
-
52
-
-
84858360749
-
-
For select X-ray data of acyclic sulfonates and δ-sultones, see: (a) Ferguson, G.; Schwan, A. L.; Kalin, M. L.; Snelgrove, J. L. Acta Crystallogr. 1997, C53, IUC9700009.
-
For select X-ray data of acyclic sulfonates and δ-sultones, see: (a) Ferguson, G.; Schwan, A. L.; Kalin, M. L.; Snelgrove, J. L. Acta Crystallogr. 1997, C53, IUC9700009.
-
-
-
-
53
-
-
33751580363
-
-
(b) Horger, R.; Marsch, M.; Geyer, A.; Harms, K. Acta Crystallogr. 2005, E61, o3447-o3448.
-
(2005)
Acta Crystallogr
, vol.E61
-
-
Horger, R.1
Marsch, M.2
Geyer, A.3
Harms, K.4
-
54
-
-
35548942816
-
-
We have used a similar argument to explain the strong bias for oxathiazinane dioxide formation in amination reactions of sulfamate esters, see ref 7a
-
We have used a similar argument to explain the strong bias for oxathiazinane dioxide formation in amination reactions of sulfamate esters, see ref 7a.
-
-
-
-
55
-
-
15044355865
-
-
(a) Ghanem, A.; Lacrampe, F.; Schurig, V. Helv. Chim. Acta 2005, 88, 216-239.
-
(2005)
Helv. Chim. Acta
, vol.88
, pp. 216-239
-
-
Ghanem, A.1
Lacrampe, F.2
Schurig, V.3
-
57
-
-
84987262316
-
-
Müller has demonstrated Rh-catalyzed C-H insertions of isolated iodonium ylides: Müller, P.; Fernandez, D. Helv. Chim. Acta 1995, 78, 947-958.
-
Müller has demonstrated Rh-catalyzed C-H insertions of isolated iodonium ylides: Müller, P.; Fernandez, D. Helv. Chim. Acta 1995, 78, 947-958.
-
-
-
-
58
-
-
9644254037
-
-
Rh2(esp)2, Rh 2(ααα′α′-tetramethyl-1, 3-benzenedipropionate)2, see: Espino, C G, Fiori, K. W, Kim, M, Du Bois, J. J. Am. Chem. Soc. 2004, 126, 15378-15379. Interestingly, syringe-pump addition of Rh2(oct)4 over a 1 h period to a suspension of 4, PhI=O, Cs2CO3, and 3 ÅMS, gave results comparable to entry 7. The unique effectiveness of Rh2(OAc)4 as a catalyst for this process is absent a clear explanation at this time
-
4 as a catalyst for this process is absent a clear explanation at this time.
-
-
-
-
60
-
-
0001411520
-
-
For reviews on sultone synthesis and reactivity, see: a
-
For reviews on sultone synthesis and reactivity, see: (a) Roberts, D. W.; Williams, D. L. Tetrahedron 1987, 43, 1027-1062.
-
(1987)
Tetrahedron
, vol.43
, pp. 1027-1062
-
-
Roberts, D.W.1
Williams, D.L.2
-
62
-
-
84858353275
-
-
3 upon heating with or without acid gave no reaction.
-
3 upon heating with or without acid gave no reaction.
-
-
-
-
63
-
-
35548959702
-
-
Use of Zn dust alone resulted in conversion to the corresponding sulfinic acid, which proved resistant toward desulfinylation
-
Use of Zn dust alone resulted in conversion to the corresponding sulfinic acid, which proved resistant toward desulfinylation.
-
-
-
-
64
-
-
0000130998
-
-
For related transformations, see: a
-
For related transformations, see: (a) Little, R. D.; Myong, S. O. Tetrahedron Lett. 1980, 21, 3339-3342
-
(1980)
Tetrahedron Lett
, vol.21
, pp. 3339-3342
-
-
Little, R.D.1
Myong, S.O.2
-
65
-
-
0000109040
-
-
(b) Hwu, J. R. J. Org. Chem. 1983, 48, 4432-4433.
-
(1983)
J. Org. Chem
, vol.48
, pp. 4432-4433
-
-
Hwu, J.R.1
-
66
-
-
0000256188
-
-
(c) Williams, D. R.; Robinson, L. A.; Amato, G. S.; Osterhout, M. H. J. Org. Chem. 1992, 57, 3740-3744.
-
(1992)
J. Org. Chem
, vol.57
, pp. 3740-3744
-
-
Williams, D.R.1
Robinson, L.A.2
Amato, G.S.3
Osterhout, M.H.4
-
67
-
-
0028855650
-
-
(d) Metz, P.; Fleischer, M.; Fröhlich, R. Tetrahedron 1995, 51, 711-732.
-
(1995)
Tetrahedron
, vol.51
, pp. 711-732
-
-
Metz, P.1
Fleischer, M.2
Fröhlich, R.3
-
68
-
-
0031855854
-
-
(e) Doye, S.; Hotopp, T.; Wartchow, R.; Winterfeldt, E. Chem. Eur. J. 1998, 4, 1480-1488.
-
(1998)
Chem. Eur. J
, vol.4
, pp. 1480-1488
-
-
Doye, S.1
Hotopp, T.2
Wartchow, R.3
Winterfeldt, E.4
-
69
-
-
1842603677
-
-
Chen, B.-C.; Zhou, P.; Davis, F. A.; Ciganek, E. Org. React. 2003, 62, 1-356.
-
(2003)
Org. React
, vol.62
, pp. 1-356
-
-
Chen, B.-C.1
Zhou, P.2
Davis, F.A.3
Ciganek, E.4
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