-
1
-
-
0001635598
-
-
For general information on enantioselective radical reactions, see: a) P. Renaud, M. Gerster, Angew. Chem. 1998, 110, 2704;
-
(1998)
Angew. Chem.
, vol.110
, pp. 2704
-
-
Renaud, P.1
Gerster, M.2
-
5
-
-
0041878683
-
-
d) M. P. Sibi, S. Manyem, J. Zimmerman, Chem. Rev. 2003, 103, 3263.
-
(2003)
Chem. Rev.
, vol.103
, pp. 3263
-
-
Sibi, M.P.1
Manyem, S.2
Zimmerman, J.3
-
6
-
-
14744278476
-
-
For selected examples of enantioselective radical addition reactions and allylations, see: a) M. P. Sibi, G. Petrovic, J. Zimmerman, J. Am. Chem. Soc. 2005, 127, 2390;
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 2390
-
-
Sibi, M.P.1
Petrovic, G.2
Zimmerman, J.3
-
7
-
-
24044519216
-
-
b) G. K. Friestad, Y. Shen, E. L. Ruggles, Angew. Chem. 2003, 115, 5215;
-
(2003)
Angew. Chem.
, vol.115
, pp. 5215
-
-
Friestad, G.K.1
Shen, Y.2
Ruggles, E.L.3
-
9
-
-
33748551971
-
-
c) M. P. Sibi, J. Zimmerman, T. Rheault, Angew. Chem. 2003, 115, 4659;
-
(2003)
Angew. Chem.
, vol.115
, pp. 4659
-
-
Sibi, M.P.1
Zimmerman, J.2
Rheault, T.3
-
11
-
-
0035897206
-
-
d) Y. Watanabe, N. Mase, R. Furue, T. Toru, Tetrahedron Lett. 2001, 42, 2981;
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 2981
-
-
Watanabe, Y.1
Mase, N.2
Furue, R.3
Toru, T.4
-
12
-
-
0033580750
-
-
e) U. Iserloh, D. P. Curran, S. Kanemasa, Tetrahedron: Asymmetry 1999, 10, 2417;
-
(1999)
Tetrahedron: Asymmetry
, vol.10
, pp. 2417
-
-
Iserloh, U.1
Curran, D.P.2
Kanemasa, S.3
-
13
-
-
0031440150
-
-
f) M. Murakata, T. Jono, Y. Mizuno, O. Hoshino, J. Am. Chem. Soc. 1997, 119, 11 713;
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 11713
-
-
Murakata, M.1
Jono, T.2
Mizuno, Y.3
Hoshino, O.4
-
15
-
-
0000822037
-
-
h) J. H. Wu, R. Radinov, N. A. Porter, J. Am. Chem. Soc. 1995, 117, 11 029.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 11029
-
-
Wu, J.H.1
Radinov, R.2
Porter, N.A.3
-
16
-
-
33748536687
-
-
For selected examples of enantioselective hydrogen-atom transfer reactions, see: a) M. P. Sibi, K. Patil, Angew. Chem. 2004, 116, 1255;
-
(2004)
Angew. Chem.
, vol.116
, pp. 1255
-
-
Sibi, M.P.1
Patil, K.2
-
18
-
-
0000784209
-
-
b) M. P. Sibi, Y. Asano, J. B. Sausker, Angew. Chem. 2001, 113, 1333;
-
(2001)
Angew. Chem.
, vol.113
, pp. 1333
-
-
Sibi, M.P.1
Asano, Y.2
Sausker, J.B.3
-
20
-
-
0033588317
-
-
c) M. Murakata, H. Tsutsui, N. Takeuchi, O. Hoshino, Tetrahedron 1999, 55, 10 295;
-
(1999)
Tetrahedron
, vol.55
, pp. 10295
-
-
Murakata, M.1
Tsutsui, H.2
Takeuchi, N.3
Hoshino, O.4
-
23
-
-
0005466990
-
-
f) M. Blumenstein, K. Schwarzkopf, J. O. Metzger, Angew. Chem. 1997, 109, 245;
-
(1997)
Angew. Chem.
, vol.109
, pp. 245
-
-
Blumenstein, M.1
Schwarzkopf, K.2
Metzger, J.O.3
-
26
-
-
0033486022
-
-
For a report on the transfer of chirality in radical cyclization, see: D. P. Curran, W. Liu, C. H.-T. Chen, J. Am. Chem. Soc. 1999, 121, 11 012.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 11012
-
-
Curran, D.P.1
Liu, W.2
Chen, C.H.-T.3
-
27
-
-
0001184545
-
-
M. Nishida, H. Hayashi, A. Nishida, N. Kawahara, Chem. Commun. 1996, 579.
-
(1996)
Chem. Commun.
, pp. 579
-
-
Nishida, M.1
Hayashi, H.2
Nishida, A.3
Kawahara, N.4
-
29
-
-
0035812385
-
-
a) D. Yang, S. Gu, Y.-L. Yan, N.-Y. Zhu, K.-K. Cheung, J. Am. Chem. Soc. 2001, 123, 8612;
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 8612
-
-
Yang, D.1
Gu, S.2
Yan, Y.-L.3
Zhu, N.-Y.4
Cheung, K.-K.5
-
30
-
-
33748552651
-
-
b) D. Yang, S. Gu, Y.-L. Yan, H.-W. Zhao, N.-Y. Zhu, Angew. Chem. 2002, 114, 3143;
-
(2002)
Angew. Chem.
, vol.114
, pp. 3143
-
-
Yang, D.1
Gu, S.2
Yan, Y.-L.3
Zhao, H.-W.4
Zhu, N.-Y.5
-
32
-
-
33748522329
-
-
c) D. Yang, B.-F. Zheng, Q. Gao, S. Gu, N.-Y. Zhu, Angew. Chem. 2006, 118, 261;
-
(2006)
Angew. Chem.
, vol.118
, pp. 261
-
-
Yang, D.1
Zheng, B.-F.2
Gao, Q.3
Gu, S.4
Zhu, N.-Y.5
-
34
-
-
0041963076
-
-
For hydroxamic acid derivatives explored as achiral templates in the Diels-Alder reaction, see: a) O. Corminboeuf, P. Renaud, Org. Lett. 2002, 4, 1731;
-
(2002)
Org. Lett.
, vol.4
, pp. 1731
-
-
Corminboeuf, O.1
Renaud, P.2
-
37
-
-
0011433132
-
-
The principal function of a Lewis acid is to control the rotamer populations of substrates; see: a) P. Renaud, T. Bourquard, M. Gerster, N. Moufid, Angew. Chem. 1994, 106, 1680;
-
(1994)
Angew. Chem.
, vol.106
, pp. 1680
-
-
Renaud, P.1
Bourquard, T.2
Gerster, M.3
Moufid, N.4
-
40
-
-
33748225421
-
-
see also reference [1a]
-
Angew. Chem. Int. Ed. Engl 1996, 35, 190; see also reference [1a].
-
(1996)
Angew. Chem. Int. Ed. Engl.
, vol.35
, pp. 190
-
-
-
41
-
-
0037415096
-
-
O. Corminboeuf, L. Quaranta, P. Renaud, M. Liu, C. P. Jasperse, M. P. Sibi, Chem. Eur. J. 2003, 9, 28.
-
(2003)
Chem. Eur. J.
, vol.9
, pp. 28
-
-
Corminboeuf, O.1
Quaranta, L.2
Renaud, P.3
Liu, M.4
Jasperse, C.P.5
Sibi, M.P.6
-
42
-
-
0242712819
-
-
M. Ueda, H. Miyabe, A. Nishimura, O. Miyata, Y. Takemoto, T. Naito, Org. Lett. 2003, 5, 3835.
-
(2003)
Org. Lett.
, vol.5
, pp. 3835
-
-
Ueda, M.1
Miyabe, H.2
Nishimura, A.3
Miyata, O.4
Takemoto, Y.5
Naito, T.6
-
45
-
-
33748568755
-
-
note
-
1H NMR study of 1a in the presence of a chiral Lewis acid is provided in the Supporting Information: a downfield shift in the chemical shifts of hydrogen atoms around the hydroxamate ester moiety was observed.
-
-
-
-
46
-
-
0000526974
-
-
For a report on a similar inversion in configuration, see: M. P. Sibi, J. Ji, J. Org. Chem. 1997, 62, 3800.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 3800
-
-
Sibi, M.P.1
Ji, J.2
-
47
-
-
0029804421
-
-
In general, the combination of phenyl-substituted bis(oxazoline) (box) ligand and zinc Lewis acid gives high selectivity, whereas the aliphatic-substituted box ligands give high selectivity in combination with magnesium Lewis acids; see: a) M. P. Sibi, J. Ji, J. Am. Chem. Soc. 1996, 118, 9200;
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 9200
-
-
Sibi, M.P.1
Ji, J.2
-
48
-
-
0001750953
-
-
b) N. A. Porter, J. H. L. Wu, G. R. Zhang, A. D. Reed, J. Org. Chem. 1997, 62, 6702;
-
(1997)
J. Org. Chem.
, vol.62
, pp. 6702
-
-
Porter, N.A.1
Wu, J.H.L.2
Zhang, G.R.3
Reed, A.D.4
-
49
-
-
33748551971
-
-
c) M. P. Sibi, J. Zimmerman, T. Rheault, Angew. Chem. 2003, 115, 4659;
-
(2003)
Angew. Chem.
, vol.115
, pp. 4659
-
-
Sibi, M.P.1
Zimmerman, J.2
Rheault, T.3
-
51
-
-
33748528085
-
-
see the Supporting Information
-
The absolute configuration at the newly formed stereocenter of 8 could not be determined. The relative configuration of trans and cis diastereomers 8 Aa was determined by NOESY experiments (see the Supporting Information).
-
-
-
-
52
-
-
33751499942
-
-
For discussions on atom-transfer cyclization, see: a) D. P. Curran, J. Tamine, J. Org. Chem. 1991, 56, 2746;
-
(1991)
J. Org. Chem.
, vol.56
, pp. 2746
-
-
Curran, D.P.1
Tamine, J.2
-
53
-
-
0000267876
-
-
b) D. P. Curran, W. Shen, J. Zhang, T. A. Heffner, J. Am. Chem. Soc. 1990, 112, 6738.
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 6738
-
-
Curran, D.P.1
Shen, W.2
Zhang, J.3
Heffner, T.A.4
-
56
-
-
15444364845
-
-
The chiral substrate of (R)-9 (81 % ee) was prepared by our method using an iridium catalyst and the pyridinebis(oxazoline)-(pybox) ligand; see: a) H. Miyabe, K. Yoshida, M. Yamauchi, Y. Takemoto, J. Org. Chem. 2005, 70, 2148;
-
(2005)
J. Org. Chem.
, vol.70
, pp. 2148
-
-
Miyabe, H.1
Yoshida, K.2
Yamauchi, M.3
Takemoto, Y.4
-
57
-
-
10044284259
-
-
b) H. Miyabe, A. Matsumura, K. Moriyama, Y. Takemoto, Org. Lett. 2004, 6, 4631.
-
(2004)
Org. Lett.
, vol.6
, pp. 4631
-
-
Miyabe, H.1
Matsumura, A.2
Moriyama, K.3
Takemoto, Y.4
-
58
-
-
33748544575
-
-
note
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Details are provided in the Supporting Information.
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