-
1
-
-
84957896342
-
-
For relevant reviews, see
-
For relevant reviews, see:
-
-
-
-
3
-
-
83755178261
-
-
M. Yus, J. González-Gõmez, F. Foubelo, Chem. Rev. 2011, 111, 7774-7854;
-
(2011)
Chem. Rev.
, vol.111
, pp. 7774-7854
-
-
Yus, M.1
González-Gõmez, J.2
Foubelo, F.3
-
4
-
-
79954533009
-
-
S. Kobayashi, Y. Mori, J. S. Fossey, M. M. Salter, Chem. Rev. 2011, 111, 2626-2704;
-
(2011)
Chem. Rev.
, vol.111
, pp. 2626-2704
-
-
Kobayashi, S.1
Mori, Y.2
Fossey, J.S.3
Salter, M.M.4
-
5
-
-
84905571261
-
-
H.-X. Huo, J. R. Duvall, M.-Y. Huang, R. Hong, Org. Chem. Front. 2014, 1, 303-320.
-
(2014)
Org. Chem. Front.
, vol.1
, pp. 303-320
-
-
Huo, H.-X.1
Duvall, J.R.2
Huang, M.-Y.3
Hong, R.4
-
6
-
-
84864877550
-
-
Y. Luo, H. B. Hepburn, N. Chotsaeng, H. W. Lam, Angew. Chem. Int. Ed. 2012, 51, 8309-8313;
-
(2012)
Angew. Chem. Int. Ed.
, vol.51
, pp. 8309-8313
-
-
Luo, Y.1
Hepburn, H.B.2
Chotsaeng, N.3
Lam, H.W.4
-
7
-
-
84873355166
-
-
Angew. Chem. 2012, 124, 8434-8438;
-
(2012)
Angew. Chem.
, vol.124
, pp. 8434-8438
-
-
-
8
-
-
84885020347
-
-
H. B. Hepburn, N. Chotsaeng, Y. Luo, H. W. Lam, Synthesis 2013, 2649-2661.
-
(2013)
Synthesis
, pp. 2649-2661
-
-
Hepburn, H.B.1
Chotsaeng, N.2
Luo, Y.3
Lam, H.W.4
-
9
-
-
84863221411
-
-
For enantioselective rhodium-catalyzed additions of alkenyltrifluoroborates to cyclic imines, see
-
For enantioselective rhodium-catalyzed additions of alkenyltrifluoroborates to cyclic imines, see:, Y. Luo, A. J. Carnell, H. W. Lam, Angew. Chem. Int. Ed. 2012, 51, 6762-6766;
-
(2012)
Angew. Chem. Int. Ed.
, vol.51
, pp. 6762-6766
-
-
Luo, Y.1
Carnell, A.J.2
Lam, H.W.3
-
10
-
-
84864877686
-
-
Angew. Chem. 2012, 124, 6866-6870.
-
(2012)
Angew. Chem.
, vol.124
, pp. 6866-6870
-
-
-
11
-
-
84957896343
-
-
For other examples of enantioselective rhodium-catalyzed additions of organoboron reagents to cyclic imines, see
-
For other examples of enantioselective rhodium-catalyzed additions of organoboron reagents to cyclic imines, see:
-
-
-
-
12
-
-
84858681579
-
-
T. Nishimura, A. Noishiki, G. Chit Tsui, T. Hayashi, J. Am. Chem. Soc. 2012, 134, 5056-5059;
-
(2012)
J. Am. Chem. Soc.
, vol.134
, pp. 5056-5059
-
-
Nishimura, T.1
Noishiki, A.2
Chit Tsui, G.3
Hayashi, T.4
-
13
-
-
84872785966
-
-
H. Wang, T. Jiang, M.-H. Xu, J. Am. Chem. Soc. 2013, 135, 971-974;
-
(2013)
J. Am. Chem. Soc.
, vol.135
, pp. 971-974
-
-
Wang, H.1
Jiang, T.2
Xu, M.-H.3
-
14
-
-
84873389352
-
-
T. Nishimura, A. Noishiki, Y. Ebe, T. Hayashi, Angew. Chem. Int. Ed. 2013, 52, 1777-1780;
-
(2013)
Angew. Chem. Int. Ed.
, vol.52
, pp. 1777-1780
-
-
Nishimura, T.1
Noishiki, A.2
Ebe, Y.3
Hayashi, T.4
-
15
-
-
84880107143
-
-
Angew. Chem. 2013, 125, 1821-1824;
-
(2013)
Angew. Chem.
, vol.125
, pp. 1821-1824
-
-
-
17
-
-
84878093558
-
-
T. Nishimura, Y. Ebe, H. Fujimoto, T. Hayashi, Chem. Commun. 2013, 49, 5504-5506;
-
(2013)
Chem. Commun.
, vol.49
, pp. 5504-5506
-
-
Nishimura, T.1
Ebe, Y.2
Fujimoto, H.3
Hayashi, T.4
-
18
-
-
84903175751
-
-
Y.-J. Chen, Y.-H. Chen, C.-G. Feng, G.-Q. Lin, Org. Lett. 2014, 16, 3400-3403;
-
(2014)
Org. Lett.
, vol.16
, pp. 3400-3403
-
-
Chen, Y.-J.1
Chen, Y.-H.2
Feng, C.-G.3
Lin, G.-Q.4
-
19
-
-
84957896344
-
-
Angew. Chem. Int. Ed., DOI:; Angew. Chem. DOI.
-
C. Jiang, Y. Lu, T. Hayashi, Angew. Chem. Int. Ed. 2014, DOI:; Angew. Chem. 2014, DOI:.
-
(2014)
-
-
Jiang, C.1
Lu, Y.2
Hayashi, T.3
-
21
-
-
77957334467
-
-
Angew. Chem. 2010, 122, 2810-2814.
-
(2010)
Angew. Chem.
, vol.122
, pp. 2810-2814
-
-
-
22
-
-
84957896345
-
-
For other catalytic enantioselective additions of allylboron compounds to imines, see
-
For other catalytic enantioselective additions of allylboron compounds to imines, see:
-
-
-
-
23
-
-
33745033537
-
-
R. Wada, T. Shibuguchi, S. Makino, K. Oisaki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2006, 128, 7687-7691;
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 7687-7691
-
-
Wada, R.1
Shibuguchi, T.2
Makino, S.3
Oisaki, K.4
Kanai, M.5
Shibasaki, M.6
-
24
-
-
34250816839
-
-
J. Aydin, K. S. Kumar, M. J. Sayah, O. A. Wallner, K. Szabõ, J. Org. Chem. 2007, 72, 4689-4697;
-
(2007)
J. Org. Chem.
, vol.72
, pp. 4689-4697
-
-
Aydin, J.1
Kumar, K.S.2
Sayah, M.J.3
Wallner, O.A.4
Szabõ, K.5
-
25
-
-
37049035131
-
-
S. Lou, P. N. Moquist, S. E. Schaus, J. Am. Chem. Soc. 2007, 129, 15398-15404;
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 15398-15404
-
-
Lou, S.1
Moquist, P.N.2
Schaus, S.E.3
-
26
-
-
44649186145
-
-
M. Kanai, R. Wada, T. Shibuguchi, M. Shibasaki, Pure Appl. Chem. 2008, 80, 1055-1062;
-
(2008)
Pure Appl. Chem.
, vol.80
, pp. 1055-1062
-
-
Kanai, M.1
Wada, R.2
Shibuguchi, T.3
Shibasaki, M.4
-
27
-
-
41449108851
-
-
M. Fujita, T. Nagano, U. Schneider, T. Hamada, C. Ogawa, S. Kobayashi, J. Am. Chem. Soc. 2008, 130, 2914-2915;
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 2914-2915
-
-
Fujita, M.1
Nagano, T.2
Schneider, U.3
Hamada, T.4
Ogawa, C.5
Kobayashi, S.6
-
28
-
-
77749292465
-
-
A. Chakrabarti, H. Konishi, M. Yamaguchi, U. Schneider, S. Kobayashi, Angew. Chem. Int. Ed. 2010, 49, 1838-1841;
-
(2010)
Angew. Chem. Int. Ed.
, vol.49
, pp. 1838-1841
-
-
Chakrabarti, A.1
Konishi, H.2
Yamaguchi, M.3
Schneider, U.4
Kobayashi, S.5
-
29
-
-
78249281525
-
-
Angew. Chem. 2010, 122, 1882-1885;
-
(2010)
Angew. Chem.
, vol.122
, pp. 1882-1885
-
-
-
30
-
-
79952583173
-
-
E. M. Vieira, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2011, 133, 3332-3335;
-
(2011)
J. Am. Chem. Soc.
, vol.133
, pp. 3332-3335
-
-
Vieira, E.M.1
Snapper, M.L.2
Hoveyda, A.H.3
-
31
-
-
81255127892
-
-
Y.-Y. Huang, A. Chakrabarti, N. Morita, U. Schneider, S. Kobayashi, Angew. Chem. Int. Ed. 2011, 50, 11121-11124;
-
(2011)
Angew. Chem. Int. Ed.
, vol.50
, pp. 11121-11124
-
-
Huang, Y.-Y.1
Chakrabarti, A.2
Morita, N.3
Schneider, U.4
Kobayashi, S.5
-
32
-
-
84863215884
-
-
Angew. Chem. 2011, 123, 11317-11320;
-
(2011)
Angew. Chem.
, vol.123
, pp. 11317-11320
-
-
-
33
-
-
84873635491
-
-
D. L. Silverio, S. Torker, T. Pilyugina, E. M. Vieira, M. L. Snapper, F. Haeffner, A. H. Hoveyda, Nature 2013, 494, 216-221.
-
(2013)
Nature
, vol.494
, pp. 216-221
-
-
Silverio, D.L.1
Torker, S.2
Pilyugina, T.3
Vieira, E.M.4
Snapper, M.L.5
Haeffner, F.6
Hoveyda, A.H.7
-
34
-
-
84957896346
-
-
The stereochemistries of products 5 b, 5 e, 11 a, 12 c, and 12 d were confirmed by X-ray crystallography. See the Supporting Information for details. The stereochemistries of the remaining products were assigned by analogy. CCDC 1013875 (5 b), 1013876 (5 e), 1013877 (12 c), 1013878 (12 d), and 1019074 (11 a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
-
The stereochemistries of products 5 b, 5 e, 11 a, 12 c, and 12 d were confirmed by X-ray crystallography. See the Supporting Information for details. The stereochemistries of the remaining products were assigned by analogy. CCDC 1013875 (5 b), 1013876 (5 e), 1013877 (12 c), 1013878 (12 d), and 1019074 (11 a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
-
-
-
-
35
-
-
84957896347
-
-
For early reports of 1,4-rhodium(I) migration, see
-
For early reports of 1,4-rhodium(I) migration, see:
-
-
-
-
36
-
-
0034715487
-
-
K. Oguma, M. Miura, T. Satoh, M. Nomura, J. Am. Chem. Soc. 2000, 122, 10464-10465;
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 10464-10465
-
-
Oguma, K.1
Miura, M.2
Satoh, T.3
Nomura, M.4
-
37
-
-
0035840942
-
-
T. Hayashi, K. Inoue, N. Taniguchi, M. Ogasawara, J. Am. Chem. Soc. 2001, 123, 9918-9919.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 9918-9919
-
-
Hayashi, T.1
Inoue, K.2
Taniguchi, N.3
Ogasawara, M.4
-
38
-
-
84957896348
-
-
For reviews of 1,4-metal migration, see
-
For reviews of 1,4-metal migration, see:
-
-
-
-
40
-
-
33745119967
-
-
Angew. Chem. 2005, 117, 7680-7685;
-
(2005)
Angew. Chem.
, vol.117
, pp. 7680-7685
-
-
-
42
-
-
84957896349
-
-
For representative examples of 1,4-rhodium migration, see
-
For representative examples of 1,4-rhodium migration, see:
-
-
-
-
44
-
-
13444306280
-
-
T. Miura, T. Sasaki, H. Nakazawa, M. Murakami, J. Am. Chem. Soc. 2005, 127, 1390-1391;
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 1390-1391
-
-
Miura, T.1
Sasaki, T.2
Nakazawa, H.3
Murakami, M.4
-
45
-
-
14844291349
-
-
R. Shintani, K. Okamoto, T. Hayashi, J. Am. Chem. Soc. 2005, 127, 2872-2873;
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 2872-2873
-
-
Shintani, R.1
Okamoto, K.2
Hayashi, T.3
-
46
-
-
14944374454
-
-
H. Yamabe, A. Mizuno, H. Kusama, N. Iwasawa, J. Am. Chem. Soc. 2005, 127, 3248-3249;
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 3248-3249
-
-
Yamabe, H.1
Mizuno, A.2
Kusama, H.3
Iwasawa, N.4
-
47
-
-
34250872754
-
-
R. Shintani, K. Takatsu, T. Hayashi, Angew. Chem. Int. Ed. 2007, 46, 3735-3737;
-
(2007)
Angew. Chem. Int. Ed.
, vol.46
, pp. 3735-3737
-
-
Shintani, R.1
Takatsu, K.2
Hayashi, T.3
-
48
-
-
53549106575
-
-
Angew. Chem. 2007, 119, 3809-3811;
-
(2007)
Angew. Chem.
, vol.119
, pp. 3809-3811
-
-
-
49
-
-
35048874634
-
-
T. Matsuda, M. Shigeno, M. Murakami, J. Am. Chem. Soc. 2007, 129, 12086-12087;
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 12086-12087
-
-
Matsuda, T.1
Shigeno, M.2
Murakami, M.3
-
50
-
-
53549084862
-
-
R. Shintani, K. Takatsu, T. Katoh, T. Nishimura, T. Hayashi, Angew. Chem. Int. Ed. 2008, 47, 1447-1449;
-
(2008)
Angew. Chem. Int. Ed.
, vol.47
, pp. 1447-1449
-
-
Shintani, R.1
Takatsu, K.2
Katoh, T.3
Nishimura, T.4
Hayashi, T.5
-
51
-
-
57849092412
-
-
Angew. Chem. 2008, 120, 1469-1471;
-
(2008)
Angew. Chem.
, vol.120
, pp. 1469-1471
-
-
-
52
-
-
57849088665
-
-
J. Panteleev, F. Menard, M. Lautens, Adv. Synth. Catal. 2008, 350, 2893-2902;
-
(2008)
Adv. Synth. Catal.
, vol.350
, pp. 2893-2902
-
-
Panteleev, J.1
Menard, F.2
Lautens, M.3
-
53
-
-
70349944361
-
-
T. Seiser, O. A. Roth, N. Cramer, Angew. Chem. Int. Ed. 2009, 48, 6320-6323;
-
(2009)
Angew. Chem. Int. Ed.
, vol.48
, pp. 6320-6323
-
-
Seiser, T.1
Roth, O.A.2
Cramer, N.3
-
54
-
-
70449563673
-
-
Angew. Chem. 2009, 121, 6438-6441;
-
(2009)
Angew. Chem.
, vol.121
, pp. 6438-6441
-
-
-
55
-
-
73349132334
-
-
M. Shigeno, T. Yamamoto, M. Murakami, Chem. Eur. J. 2009, 15, 12929-12931;
-
(2009)
Chem. Eur. J.
, vol.15
, pp. 12929-12931
-
-
Shigeno, M.1
Yamamoto, T.2
Murakami, M.3
-
56
-
-
77952661755
-
-
R. Shintani, S. Isobe, M. Takeda, T. Hayashi, Angew. Chem. Int. Ed. 2010, 49, 3795-3798;
-
(2010)
Angew. Chem. Int. Ed.
, vol.49
, pp. 3795-3798
-
-
Shintani, R.1
Isobe, S.2
Takeda, M.3
Hayashi, T.4
-
57
-
-
84555167041
-
-
Angew. Chem. 2010, 122, 3883-3886;
-
(2010)
Angew. Chem.
, vol.122
, pp. 3883-3886
-
-
-
59
-
-
80051759005
-
-
Angew. Chem. 2010, 122, 10361-10365;
-
(2010)
Angew. Chem.
, vol.122
, pp. 10361-10365
-
-
-
61
-
-
84857616911
-
-
T. Matsuda, Y. Suda, A. Takahashi, Chem. Commun. 2012, 48, 2988-2990;
-
(2012)
Chem. Commun.
, vol.48
, pp. 2988-2990
-
-
Matsuda, T.1
Suda, Y.2
Takahashi, A.3
-
62
-
-
84858064539
-
-
K. Sasaki, T. Nishimura, R. Shintani, E. A. B. Kantchev, T. Hayashi, Chem. Sci. 2012, 3, 1278-1283;
-
(2012)
Chem. Sci.
, vol.3
, pp. 1278-1283
-
-
Sasaki, K.1
Nishimura, T.2
Shintani, R.3
Kantchev, E.A.B.4
Hayashi, T.5
-
63
-
-
84887127030
-
-
Y. Ikeda, K. Takano, S. Kodama, Y. Ishii, Chem. Commun. 2013, 49, 11104-11106;
-
(2013)
Chem. Commun.
, vol.49
, pp. 11104-11106
-
-
Ikeda, Y.1
Takano, K.2
Kodama, S.3
Ishii, Y.4
-
64
-
-
84900452561
-
-
Y. Ikeda, K. Takano, M. Waragai, S. Kodama, N. Tsuchida, K. Takano, Y. Ishii, Organometallics 2014, 33, 2142-2145;
-
(2014)
Organometallics
, vol.33
, pp. 2142-2145
-
-
Ikeda, Y.1
Takano, K.2
Waragai, M.3
Kodama, S.4
Tsuchida, N.5
Takano, K.6
Ishii, Y.7
-
65
-
-
84957896350
-
-
Angew. Chem. Int. Ed., DOI:; Angew. Chem., DOI.
-
D. J. Burns, H. W. Lam, Angew. Chem. Int. Ed. 2014, DOI:; Angew. Chem. 2014, DOI:.
-
(2014)
-
-
Burns, D.J.1
Lam, H.W.2
-
66
-
-
33745535959
-
-
Y. Takada, S. Hayashi, K. Hirano, H. Yorimitsu, K. Oshima, Org. Lett. 2006, 8, 2515-2517;
-
(2006)
Org. Lett.
, vol.8
, pp. 2515-2517
-
-
Takada, Y.1
Hayashi, S.2
Hirano, K.3
Yorimitsu, H.4
Oshima, K.5
-
67
-
-
40649116007
-
-
Y. Sumida, Y. Takada, S. Hayashi, K. Hirano, H. Yorimitsu, K. Oshima, Chem. Asian J. 2008, 3, 119-125.
-
(2008)
Chem. Asian J.
, vol.3
, pp. 119-125
-
-
Sumida, Y.1
Takada, Y.2
Hayashi, S.3
Hirano, K.4
Yorimitsu, H.5
Oshima, K.6
-
68
-
-
84957896351
-
-
Other cyclic imines 18, 20, and 21 were not suitable substrates in these reactions. Imine 18 reacted with prenyltrifluoroborate 2 a under the conditions shown in Table 1 to provide what appeared to be 19 in only ≈4 % conversion, with the remaining mass balance being unreacted 18. Imines 20 and 21 were completely unreactive.
-
Other cyclic imines 18, 20, and 21 were not suitable substrates in these reactions. Imine 18 reacted with prenyltrifluoroborate 2 a under the conditions shown in Table 1 to provide what appeared to be 19 in only ≈4 % conversion, with the remaining mass balance being unreacted 18. Imines 20 and 21 were completely unreactive.
-
-
-
-
69
-
-
84957896352
-
-
Attempted reactions of 2 f with imine 4 a led to no traces of any allylation products.
-
Attempted reactions of 2 f with imine 4 a led to no traces of any allylation products.
-
-
-
-
70
-
-
84957896353
-
-
Reviews of chiral dienes
-
Reviews of chiral dienes:
-
-
-
-
74
-
-
48249145636
-
-
Angew. Chem. 2008, 120, 852-884;
-
(2008)
Angew. Chem.
, vol.120
, pp. 852-884
-
-
-
75
-
-
49049101971
-
-
C. Defieber, H. Grutzmacher, E. M. Carreira, Angew. Chem. Int. Ed. 2008, 47, 4482-4502;
-
(2008)
Angew. Chem. Int. Ed.
, vol.47
, pp. 4482-4502
-
-
Defieber, C.1
Grutzmacher, H.2
Carreira, E.M.3
-
76
-
-
54749086828
-
-
Angew. Chem. 2008, 120, 4558-4579.
-
(2008)
Angew. Chem.
, vol.120
, pp. 4558-4579
-
-
-
77
-
-
84957896354
-
-
Diene ent- L1 (see Scheme 1a) gave a 71:29 mixture of ent- 5 a and ent- 6 a, and ent- 5 a was formed in 98 % ee. However, the conversion of this reaction was only 65 %. Diene L3 (Ref. [18]) gave a 36:64 mixture of ent- 5 a and ent- 6 a in 85 % conversion (ee values not determined).
-
Diene ent- L1 (see Scheme 1a) gave a 71:29 mixture of ent- 5 a and ent- 6 a, and ent- 5 a was formed in 98 % ee. However, the conversion of this reaction was only 65 %. Diene L3 (Ref. [18]) gave a 36:64 mixture of ent- 5 a and ent- 6 a in 85 % conversion (ee values not determined).
-
-
-
-
79
-
-
84957896355
-
-
The absolute configurations of the products in Scheme 6 were assigned by analogy with the stereochemical outcomes obtained in previous studies (see Ref. [2]).
-
The absolute configurations of the products in Scheme 6 were assigned by analogy with the stereochemical outcomes obtained in previous studies (see Ref. [2]).
-
-
-
-
80
-
-
6444231736
-
-
N. Tokunaga, Y. Otomaru, K. Okamoto, K. Ueyama, R. Shintani, T. Hayashi, J. Am. Chem. Soc. 2004, 126, 13584-13585;
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 13584-13585
-
-
Tokunaga, N.1
Otomaru, Y.2
Okamoto, K.3
Ueyama, K.4
Shintani, R.5
Hayashi, T.6
-
81
-
-
17044390818
-
-
Y. Otomaru, K. Okamoto, R. Shintani, T. Hayashi, J. Org. Chem. 2005, 70, 2503-2508.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 2503-2508
-
-
Otomaru, Y.1
Okamoto, K.2
Shintani, R.3
Hayashi, T.4
-
82
-
-
0032503512
-
-
The enyl (σ+π) character of the allylrhodium(I) species could also be invoked in our reactions described herein. For evidence of the enyl (σ+π) character of the allylrhodium(III) species, see.
-
The enyl (σ+π) character of the allylrhodium(I) species could also be invoked in our reactions described herein. For evidence of the enyl (σ+π) character of the allylrhodium(III) species, see:, P. A. Evans, J. D. Nelson, J. Am. Chem. Soc. 1998, 120, 5581-5582.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 5581-5582
-
-
Evans, P.A.1
Nelson, J.D.2
|