-
1
-
-
85043140598
-
-
For reviews on different strategies of catalytic asymmetric C−H functionalization, see
-
For reviews on different strategies of catalytic asymmetric C−H functionalization, see:
-
-
-
-
3
-
-
70350494926
-
-
R. Giri, B.-F. Shi, K. M. Engle, N. Maugel, J.-Q. Yu, Chem. Soc. Rev. 2009, 38, 3242–3272;
-
(2009)
Chem. Soc. Rev.
, vol.38
, pp. 3242-3272
-
-
Giri, R.1
Shi, B.-F.2
Engle, K.M.3
Maugel, N.4
Yu, J.-Q.5
-
4
-
-
77349105953
-
-
M. P. Doyle, R. Duffy, M. Ratnikov, L. Zhou, Chem. Rev. 2010, 110, 704–724;
-
(2010)
Chem. Rev.
, vol.110
, pp. 704-724
-
-
Doyle, M.P.1
Duffy, R.2
Ratnikov, M.3
Zhou, L.4
-
5
-
-
84890902110
-
-
S. A. Girard, T. Knauber, C.-J. Li, Angew. Chem. Int. Ed. 2014, 53, 74–100;
-
(2014)
Angew. Chem. Int. Ed.
, vol.53
, pp. 74-100
-
-
Girard, S.A.1
Knauber, T.2
Li, C.-J.3
-
6
-
-
84896391244
-
-
Angew. Chem. 2014, 126, 76–103;
-
(2014)
Angew. Chem.
, vol.126
, pp. 76-103
-
-
-
10
-
-
57249084541
-
-
J. Robertson, J. Pillai, R. K. Lush, Chem. Soc. Rev. 2001, 30, 94–103;
-
(2001)
Chem. Soc. Rev.
, vol.30
, pp. 94-103
-
-
Robertson, J.1
Pillai, J.2
Lush, R.K.3
-
11
-
-
0344667717
-
-
A. Gansäuer, T. Lauterbach, S. Narayan, Angew. Chem. Int. Ed. 2003, 42, 5556–5573;
-
(2003)
Angew. Chem. Int. Ed.
, vol.42
, pp. 5556-5573
-
-
Gansäuer, A.1
Lauterbach, T.2
Narayan, S.3
-
12
-
-
4544294120
-
-
Angew. Chem. 2003, 115, 5714–5731;
-
(2003)
Angew. Chem.
, vol.115
, pp. 5714-5731
-
-
-
15
-
-
76849105694
-
-
J. Sperry, Y.-C. Liu, M. A. Brimble, Org. Biomol. Chem. 2010, 8, 29–38;
-
(2010)
Org. Biomol. Chem.
, vol.8
, pp. 29-38
-
-
Sperry, J.1
Liu, Y.-C.2
Brimble, M.A.3
-
17
-
-
84923368114
-
-
Angew. Chem. 2014, 126, 5110–5137;
-
(2014)
Angew. Chem.
, vol.126
, pp. 5110-5137
-
-
-
18
-
-
84915746305
-
-
M. Nechab, S. Mondal, M. P. Bertrand, Chem. Eur. J. 2014, 20, 16034–16059.
-
(2014)
Chem. Eur. J.
, vol.20
, pp. 16034-16059
-
-
Nechab, M.1
Mondal, S.2
Bertrand, M.P.3
-
19
-
-
84880124916
-
-
C. K. Prier, D. A. Rankic, D. W. C. MacMillan, Chem. Rev. 2013, 113, 5322–5363;
-
(2013)
Chem. Rev.
, vol.113
, pp. 5322-5363
-
-
Prier, C.K.1
Rankic, D.A.2
MacMillan, D.W.C.3
-
21
-
-
84880378120
-
-
Angew. Chem. 2013, 125, 4832–4842;
-
(2013)
Angew. Chem.
, vol.125
, pp. 4832-4842
-
-
-
22
-
-
84896340900
-
-
F. Dénès, M. Pichowicz, G. Povie, P. Renaud, Chem. Rev. 2014, 114, 2587–2693;
-
(2014)
Chem. Rev.
, vol.114
, pp. 2587-2693
-
-
Dénès, F.1
Pichowicz, M.2
Povie, G.3
Renaud, P.4
-
24
-
-
84967318126
-
-
J.-R. Chen, X.-Q. Hu, L.-Q. Lu, W.-J. Xiao, Chem. Soc. Rev. 2016, 45, 2044–2056.
-
(2016)
Chem. Soc. Rev.
, vol.45
, pp. 2044-2056
-
-
Chen, J.-R.1
Hu, X.-Q.2
Lu, L.-Q.3
Xiao, W.-J.4
-
25
-
-
84955709299
-
-
J. Zhang, Y. Li, F. Zhang, C. Hu, Y. Chen, Angew. Chem. Int. Ed. 2016, 55, 1872–1875;
-
(2016)
Angew. Chem. Int. Ed.
, vol.55
, pp. 1872-1875
-
-
Zhang, J.1
Li, Y.2
Zhang, F.3
Hu, C.4
Chen, Y.5
-
26
-
-
84977497497
-
-
Angew. Chem. 2016, 128, 1904–1907.
-
(2016)
Angew. Chem.
, vol.128
, pp. 1904-1907
-
-
-
27
-
-
82355182535
-
-
For photoinduced electron-transfer-promoted redox fragmentation of N-alkoxyphthalimides, see also
-
For photoinduced electron-transfer-promoted redox fragmentation of N-alkoxyphthalimides, see also: M. Zlotorzynska, G. M. Sammis, Org. Lett. 2011, 13, 6264–6267.
-
(2011)
Org. Lett.
, vol.13
, pp. 6264-6267
-
-
Zlotorzynska, M.1
Sammis, G.M.2
-
28
-
-
0000579114
-
-
For the first report on N-alkoxyphthalimides for the generation of alkoxyl radicals, see
-
For the first report on N-alkoxyphthalimides for the generation of alkoxyl radicals, see: S. Kim, T. A. Lee, Y. Song, Synlett 1998, 471–472.
-
(1998)
Synlett
, pp. 471-472
-
-
Kim, S.1
Lee, T.A.2
Song, Y.3
-
29
-
-
0001279669
-
-
D. P. Curran, D. Kim, H. T. Liu, W. Shen, J. Am. Chem. Soc. 1988, 110, 5900–5902;
-
(1988)
J. Am. Chem. Soc.
, vol.110
, pp. 5900-5902
-
-
Curran, D.P.1
Kim, D.2
Liu, H.T.3
Shen, W.4
-
31
-
-
0141570904
-
-
For a review on radical translocations initiated by alkoxyl radicals, see
-
For a review on radical translocations initiated by alkoxyl radicals, see: Ž. Čeković, Tetrahedron 2003, 59, 8073–8090.
-
(2003)
Tetrahedron
, vol.59
, pp. 8073-8090
-
-
Čeković, Ž.1
-
32
-
-
85043142277
-
-
For seminal work on chiral Lewis acid catalysis for conjugate radical additions, see
-
For seminal work on chiral Lewis acid catalysis for conjugate radical additions, see:
-
-
-
-
33
-
-
0029804421
-
-
M. P. Sibi, J. Ji, J. H. Wu, S. Gürtler, N. A. Porter, J. Am. Chem. Soc. 1996, 118, 9200–9201;
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 9200-9201
-
-
Sibi, M.P.1
Ji, J.2
Wu, J.H.3
Gürtler, S.4
Porter, N.A.5
-
35
-
-
0004145743
-
-
VCH, Weinheim
-
D. P. Curran, N. A. Porter, B. Giese, Stereochemistry of Radical Reactions, VCH, Weinheim, 1996.
-
(1996)
Stereochemistry of Radical Reactions
-
-
Curran, D.P.1
Porter, N.A.2
Giese, B.3
-
36
-
-
85043119030
-
-
For reviews on enantioselective radical reactions, see
-
For reviews on enantioselective radical reactions, see:
-
-
-
-
37
-
-
0041878683
-
-
M. P. Sibi, S. Manyem, J. Zimmerman, Chem. Rev. 2003, 103, 3263–3296;
-
(2003)
Chem. Rev.
, vol.103
, pp. 3263-3296
-
-
Sibi, M.P.1
Manyem, S.2
Zimmerman, J.3
-
39
-
-
84955172566
-
-
For a recent review on the catalysis of radical reactions, including asymmetric catalysis, see
-
For a recent review on the catalysis of radical reactions, including asymmetric catalysis, see: A. Studer, D. P. Curran, Angew. Chem. Int. Ed. 2016, 55, 58–102;
-
(2016)
Angew. Chem. Int. Ed.
, vol.55
, pp. 58-102
-
-
Studer, A.1
Curran, D.P.2
-
40
-
-
84971406747
-
-
Angew. Chem. 2016, 128, 58–106.
-
(2016)
Angew. Chem.
, vol.128
, pp. 58-106
-
-
-
41
-
-
84922773549
-
-
H. Huo, X. Shen, C. Wang, L. Zhang, P. Röse, L.-A. Chen, K. Harms, M. Marsch, G. Hilt, E. Meggers, Nature 2014, 515, 100–103;
-
(2014)
Nature
, vol.515
, pp. 100-103
-
-
Huo, H.1
Shen, X.2
Wang, C.3
Zhang, L.4
Röse, P.5
Chen, L.-A.6
Harms, K.7
Marsch, M.8
Hilt, G.9
Meggers, E.10
-
42
-
-
84938840938
-
-
H. Huo, C. Wang, K. Harms, E. Meggers, J. Am. Chem. Soc. 2015, 137, 9551–9554;
-
(2015)
J. Am. Chem. Soc.
, vol.137
, pp. 9551-9554
-
-
Huo, H.1
Wang, C.2
Harms, K.3
Meggers, E.4
-
43
-
-
84957812099
-
-
C. Wang, J. Qin, X. Shen, R. Riedel, K. Harms, E. Meggers, Angew. Chem. Int. Ed. 2016, 55, 685–688;
-
(2016)
Angew. Chem. Int. Ed.
, vol.55
, pp. 685-688
-
-
Wang, C.1
Qin, J.2
Shen, X.3
Riedel, R.4
Harms, K.5
Meggers, E.6
-
44
-
-
84977082596
-
-
Angew. Chem. 2016, 128, 695–698.
-
(2016)
Angew. Chem.
, vol.128
, pp. 695-698
-
-
-
45
-
-
84921695025
-
-
C. Wang, L.-A. Chen, H. Huo, X. Shen, K. Harms, L. Gong, E. Meggers, Chem. Sci. 2015, 6, 1094–1100.
-
(2015)
Chem. Sci.
, vol.6
, pp. 1094-1100
-
-
Wang, C.1
Chen, L.-A.2
Huo, H.3
Shen, X.4
Harms, K.5
Gong, L.6
Meggers, E.7
-
46
-
-
85043121980
-
-
For dual photoredox catalysis, see
-
For dual photoredox catalysis, see:
-
-
-
-
47
-
-
84897915531
-
-
M. N. Hopkinson, B. Sahoo, J.-L. Li, F. Glorius, Chem. Eur. J. 2014, 20, 3874–3886;
-
(2014)
Chem. Eur. J.
, vol.20
, pp. 3874-3886
-
-
Hopkinson, M.N.1
Sahoo, B.2
Li, J.-L.3
Glorius, F.4
-
48
-
-
84979578174
-
-
K. L. Skubi, T. R. Blum, T. P. Yoon, Chem. Rev. 2016, 116, 10035–10074;
-
(2016)
Chem. Rev.
, vol.116
, pp. 10035-10074
-
-
Skubi, K.L.1
Blum, T.R.2
Yoon, T.P.3
-
49
-
-
84962339746
-
-
Y.-Y. Gui, L. Sun, Z.-P. Lu, D.-G. Yu, Org. Chem. Front. 2016, 3, 522–526.
-
(2016)
Org. Chem. Front.
, vol.3
, pp. 522-526
-
-
Gui, Y.-Y.1
Sun, L.2
Lu, Z.-P.3
Yu, D.-G.4
-
50
-
-
84969930961
-
-
J. Ma, X. Shen, K. Harms, E. Meggers, Dalton Trans. 2016, 45, 8320–8323.
-
(2016)
Dalton Trans.
, vol.45
, pp. 8320-8323
-
-
Ma, J.1
Shen, X.2
Harms, K.3
Meggers, E.4
-
51
-
-
84974782321
-
-
For a recent example in which we combined this rhodium-based Lewis acid catalyst with an additional photoredox sensitizer, see
-
For a recent example in which we combined this rhodium-based Lewis acid catalyst with an additional photoredox sensitizer, see: H. Huo, K. Harms, E. Meggers, J. Am. Chem. Soc. 2016, 138, 6936–6939.
-
(2016)
J. Am. Chem. Soc.
, vol.138
, pp. 6936-6939
-
-
Huo, H.1
Harms, K.2
Meggers, E.3
-
52
-
-
85043123684
-
-
See the Supporting Information for additional experiments regarding the dependence of enantioselectivity with the light source and intensity
-
See the Supporting Information for additional experiments regarding the dependence of enantioselectivity with the light source and intensity.
-
-
-
-
53
-
-
85043099497
-
-
For a related observation and interpretation, see Ref. [4]. For photoinduced electron transfer by direct excitation of Hantzsch ester with visible light, see also
-
For a related observation and interpretation, see Ref. [4]. For photoinduced electron transfer by direct excitation of Hantzsch ester with visible light, see also:
-
-
-
-
54
-
-
0032761362
-
-
X.-Q. Zhu, Y.-C. Liu, J.-P. Cheng, J. Org. Chem. 1999, 64, 8980–8981;
-
(1999)
J. Org. Chem.
, vol.64
, pp. 8980-8981
-
-
Zhu, X.-Q.1
Liu, Y.-C.2
Cheng, J.-P.3
-
55
-
-
84954360219
-
-
J. Jung, J. Kim, G. Park, Y.-M. You, E. J. Cho, Adv. Synth. Catal. 2016, 358, 74–80;
-
(2016)
Adv. Synth. Catal.
, vol.358
, pp. 74-80
-
-
Jung, J.1
Kim, J.2
Park, G.3
You, Y.-M.4
Cho, E.J.5
-
56
-
-
84977477587
-
-
W. Chen, H. Tao, W. Huang, G. Qang, S. Li, X. Cheng, G. Li, Chem. Eur. J. 2016, 22, 9546–9550.
-
(2016)
Chem. Eur. J.
, vol.22
, pp. 9546-9550
-
-
Chen, W.1
Tao, H.2
Huang, W.3
Qang, G.4
Li, S.5
Cheng, X.6
Li, G.7
-
57
-
-
0037450133
-
-
X.-Q. Zhu, H.-R. Li, Q. Li, T. Ai, J.-Y. Lu, Y. Yang, J.-P. Cheng, Chem. Eur. J. 2003, 9, 871–880;
-
(2003)
Chem. Eur. J.
, vol.9
, pp. 871-880
-
-
Zhu, X.-Q.1
Li, H.-R.2
Li, Q.3
Ai, T.4
Lu, J.-Y.5
Yang, Y.6
Cheng, J.-P.7
-
58
-
-
84911480261
-
-
A. Singh, K. Teegardin, M. Kelly, K. S. Prasad, S. Krishnan, J. D. Weaver, J. Organomet. Chem. 2015, 776, 51–59.
-
(2015)
J. Organomet. Chem.
, vol.776
, pp. 51-59
-
-
Singh, A.1
Teegardin, K.2
Kelly, M.3
Prasad, K.S.4
Krishnan, S.5
Weaver, J.D.6
-
59
-
-
0036360649
-
-
For a review on the reactivity of alkoxy radicals, see
-
For a review on the reactivity of alkoxy radicals, see: J. Hartung, T. Gottwald, K. Špehar, Synthesis 2002, 1469–1498.
-
(2002)
Synthesis
, pp. 1469-1498
-
-
Hartung, J.1
Gottwald, T.2
Špehar, K.3
-
60
-
-
85043103393
-
-
For selected recent examples on 1,5-HAT initiated by alkoxyl radicals, see
-
For selected recent examples on 1,5-HAT initiated by alkoxyl radicals, see:
-
-
-
-
61
-
-
0037131158
-
-
C. G. Francisco, A. J. Herrera, E. Suárez, J. Org. Chem. 2002, 67, 7439–7445;
-
(2002)
J. Org. Chem.
, vol.67
, pp. 7439-7445
-
-
Francisco, C.G.1
Herrera, A.J.2
Suárez, E.3
-
62
-
-
65549100154
-
-
H. Zhu, J. G. Wickenden, N. E. Campbell, J. C. T. Leung, K. M. Johnson, G. M. Sammis, Org. Lett. 2009, 11, 2019–2022;
-
(2009)
Org. Lett.
, vol.11
, pp. 2019-2022
-
-
Zhu, H.1
Wickenden, J.G.2
Campbell, N.E.3
Leung, J.C.T.4
Johnson, K.M.5
Sammis, G.M.6
-
64
-
-
84921303914
-
-
H. Zhu, J. C. T. Leung, G. M. Sammis, J. Org. Chem. 2015, 80, 965–979.
-
(2015)
J. Org. Chem.
, vol.80
, pp. 965-979
-
-
Zhu, H.1
Leung, J.C.T.2
Sammis, G.M.3
-
65
-
-
85043119793
-
-
This furthermore supports our proposed mechanism and can be explained by a competing undesired reduction of the initial oxygen- or carbon-centered radicals. See the Supporting Information for more details
-
For the relatively sluggish conversion 1 a+2 h→3 s (Figure 2) we were able to isolate 2-((1-tosylazetidin-3-yl)oxy)ethanol as a side product. This furthermore supports our proposed mechanism and can be explained by a competing undesired reduction of the initial oxygen- or carbon-centered radicals. See the Supporting Information for more details.
-
For the relatively sluggish conversion 1 a+2 h→3 s (Figure 2) we were able to isolate 2-((1-tosylazetidin-3-yl)oxy)ethanol as a side product
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