-
4
-
-
0001521573
-
-
(a) Ugi, I.; Meyr, R.; Fetzer, U.; Steinbrückner, C. Angew. Chem. 1959, 71, 386.
-
(1959)
Angew. Chem.
, vol.71
, pp. 386
-
-
Ugi, I.1
Meyr, R.2
Fetzer, U.3
Steinbrückner, C.4
-
6
-
-
26844537872
-
-
For recent reviews, see: (a) Banfi, L.; Riva, R. Org. React. 2005, 65, 1-140.
-
(2005)
Org. React.
, vol.65
, pp. 1-140
-
-
Banfi, L.1
Riva, R.2
-
10
-
-
0034665244
-
-
(e) Bienayme, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321-3329.
-
(2000)
Chem. Eur. J.
, vol.6
, pp. 3321-3329
-
-
Bienayme, H.1
Hulme, C.2
Oddon, G.3
Schmitt, P.4
-
11
-
-
2542509173
-
-
(f) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3169-3210.
-
(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 3169-3210
-
-
Dömling, A.1
Ugi, I.2
-
12
-
-
0000512227
-
-
(g) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123-131.
-
(1996)
Acc. Chem. Res.
, vol.29
, pp. 123-131
-
-
Armstrong, R.W.1
Combs, A.P.2
Tempest, P.A.3
Brown, S.D.4
Keating, T.A.5
-
13
-
-
0035801852
-
-
For recent applications of Passerini reactions, see: (a) Owens, T. D.; Araldi, G.-L.; Nutt, R. F.; Semple, J. E. Tetrahedron Lett. 2001, 42, 6271-6274.
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 6271-6274
-
-
Owens, T.D.1
Araldi, G.-L.2
Nutt, R.F.3
Semple, J.E.4
-
15
-
-
0035817974
-
-
Beck, B.; Magnin-Lachaux, M.; Herdtweck, E.; Dömling, A. Org. Lett. 2001, 3, 2875-2878.
-
(2001)
Org. Lett.
, vol.3
, pp. 2875-2878
-
-
Beck, B.1
Magnin-Lachaux, M.2
Herdtweck, E.3
Dömling, A.4
-
17
-
-
0034618307
-
-
(e) Semple, J. D.; Owens, T. D.; Nguyen, K.; Levy, O. E. Org. Lett. 2000, 2, 2769-2772.
-
(2000)
Org. Lett.
, vol.2
, pp. 2769-2772
-
-
Semple, J.D.1
Owens, T.D.2
Nguyen, K.3
Levy, O.E.4
-
18
-
-
0037182202
-
-
(f) Banfi, L.; Guanti, G.; Riva, R.; Basso, A.; Calcagno, E. Tetrahedron Lett. 2002, 43, 4067-4069.
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 4067-4069
-
-
Banfi, L.1
Guanti, G.2
Riva, R.3
Basso, A.4
Calcagno, E.5
-
19
-
-
2342485673
-
-
Cuny, G.; Gámez-Montaño, R.; Zhu, J. Tetrahedron 2004, 60, 4879-4885.
-
(2004)
Tetrahedron
, vol.60
, pp. 4879-4885
-
-
Cuny, G.1
Gámez-Montaño, R.2
Zhu, J.3
-
20
-
-
0001451826
-
-
For additions to chiral imines with ferrocenyl auxiliaries, see: (a) Ugi, I.; Offermann, K. Angew. Chem. 1963, 75, 917;
-
(1963)
Angew. Chem.
, vol.75
, pp. 917
-
-
Ugi, I.1
Offermann, K.2
-
22
-
-
0005196531
-
-
(b) Ugi, I.; Offermann, K.; Herlinger, H. Angew. Chem. 1964, 76, 613;
-
(1964)
Angew. Chem.
, vol.76
, pp. 613
-
-
Ugi, I.1
Offermann, K.2
Herlinger, H.3
-
24
-
-
0016414649
-
-
Urban, R.; Ugi, I. Angew. Chem., Int. Ed. Engl. 1975, 14, 61-62.
-
(1975)
Angew. Chem., Int. Ed. Engl.
, vol.14
, pp. 61-62
-
-
Urban, R.1
Ugi, I.2
-
25
-
-
0016987417
-
-
Eberle, G.; Ugi, I. Angew. Chem., Int. Ed. Engl. 1976, 15, 492-493.
-
(1976)
Angew. Chem., Int. Ed. Engl.
, vol.15
, pp. 492-493
-
-
Eberle, G.1
Ugi, I.2
-
26
-
-
84982338009
-
-
(e) Ugi, I.; Offermann, K.; Herlginer, H.; Marquarding, D. Justus Liebigs Ann. Chem. 1967, 709, 1-10.
-
(1967)
Justus Liebigs Ann. Chem.
, vol.709
, pp. 1-10
-
-
Ugi, I.1
Offermann, K.2
Herlginer, H.3
Marquarding, D.4
-
28
-
-
0001697647
-
-
For additions to chiral imines with carbohydrate auxiliaries, see: (a) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem. 2000, 112, 1489-1491;
-
(2000)
Angew. Chem.
, vol.112
, pp. 1489-1491
-
-
Oertel, K.1
Zech, G.2
Kunz, H.3
-
32
-
-
38849119887
-
-
Kunz, H.; Pfrengle, W.; Sager, W. Tetrahedron Lett. 1989, 30, 4109-4110.
-
(1989)
Tetrahedron Lett.
, vol.30
, pp. 4109-4110
-
-
Kunz, H.1
Pfrengle, W.2
Sager, W.3
-
33
-
-
0025949523
-
-
(e) Kunz, H.; Pfrengle, W.; Ruck, K.; Sager, W. Synthesis 1991, 1039-1042.
-
(1991)
Synthesis
, pp. 1039-1042
-
-
Kunz, H.1
Pfrengle, W.2
Ruck, K.3
Sager, W.4
-
36
-
-
0001574416
-
-
(h) Lehnhoff, S.; Goebel, M.; Karl, R. M.; Klosel, R.; Ugi, I. Angew. Chem. 1995, 107, 1208-1211;
-
(1995)
Angew. Chem.
, vol.107
, pp. 1208-1211
-
-
Lehnhoff, S.1
Goebel, M.2
Karl, R.M.3
Klosel, R.4
Ugi, I.5
-
38
-
-
28044439026
-
-
Ross, G. F.; Herdtweck, E.; Ugi, I. Tetrahedron 2002, 58, 6172-6133.
-
(2002)
Tetrahedron
, vol.58
, pp. 6172-16133
-
-
Ross, G.F.1
Herdtweck, E.2
Ugi, I.3
-
39
-
-
0009959172
-
-
For additions to chiral imines with α-methylbenzylamine auxiliary, see: (a) Divanfard, H. R.; Lysenko, Z.; Wang, P. C.; Joullie, M. M. Synth. Commun. 1978, 8, 269-273.
-
(1978)
Synth. Commun.
, vol.8
, pp. 269-273
-
-
Divanfard, H.R.1
Lysenko, Z.2
Wang, P.C.3
Joullie, M.M.4
-
40
-
-
0019186783
-
-
(b) Semple, J. E.; Wang, P. C.; Lysenko, Z.; Joullie, M. M. J. Am. Chem. Soc. 1980, 102, 7505-7510.
-
(1980)
J. Am. Chem. Soc.
, vol.102
, pp. 7505-7510
-
-
Semple, J.E.1
Wang, P.C.2
Lysenko, Z.3
Joullie, M.M.4
-
41
-
-
2742610388
-
-
For addition of a chiral isocyanide to aldehydes and imines, see: Bock, H.; Ugi, I. J. Prakt. Chem. 1997, 339, 385-389.
-
(1997)
J. Prakt. Chem.
, vol.339
, pp. 385-389
-
-
Bock, H.1
Ugi, I.2
-
42
-
-
0001678717
-
-
Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg; Chapter 28
-
(a) Mori, A.; Inoue, S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, 1999; Vol. II; Chapter 28.
-
(1999)
Comprehensive Asymmetric Catalysis
, vol.2
-
-
Mori, A.1
Inoue, S.2
-
43
-
-
0041378065
-
-
(b) Groger, H. Chem. Rev. 2003, 103, 2795-2827.
-
(2003)
Chem. Rev.
, vol.103
, pp. 2795-2827
-
-
Groger, H.1
-
44
-
-
0043071355
-
-
(a) Frey, R.; Galbraith, S. G.; Guelfi, S.; Lamberth, C.; Zeller, M. Synlett 2003, 1536-1538.
-
(2003)
Synlett
, pp. 1536-1538
-
-
Frey, R.1
Galbraith, S.G.2
Guelfi, S.3
Lamberth, C.4
Zeller, M.5
-
45
-
-
9444230492
-
-
(b) Andreana, P.; Liu, C. C.; Schreiber, S. L. Org. Lett. 2004, 5, 4231-4233.
-
(2004)
Org. Lett.
, vol.5
, pp. 4231-4233
-
-
Andreana, P.1
Liu, C.C.2
Schreiber, S.L.3
-
46
-
-
84982336930
-
-
For early examples of Lewis acid promoted α-addition reaction of isocyanides, see: (a) Muller, E.; Zeeh, B. Liebigs Ann. Chem. 1966, 696, 72-80.
-
(1966)
Liebigs Ann. Chem.
, vol.696
, pp. 72-80
-
-
Muller, E.1
Zeeh, B.2
-
48
-
-
0038801722
-
-
Saegusa, T.; Taka-Ishi, N.; Fujii, H. Tetrahedron 1968, 24, 3795-3798.
-
(1968)
Tetrahedron
, vol.24
, pp. 3795-3798
-
-
Saegusa, T.1
Taka-Ishi, N.2
Fujii, H.3
-
50
-
-
84985648238
-
-
(e) Seebach, D.; Adam, G.; Gees, T.; Schiess, M.; Weigand, W. Chem. Ber. 1988, 121, 507-517.
-
(1988)
Chem. Ber.
, vol.121
, pp. 507-517
-
-
Seebach, D.1
Adam, G.2
Gees, T.3
Schiess, M.4
Weigand, W.5
-
51
-
-
33751385281
-
-
(f) Carofiglio, T.; Cozzi, P. G.; Floriani, C.; Chiesa-Villa, A.; Rizzoli, C. Organometallics 1993, 12, 2726-2736.
-
(1993)
Organometallics
, vol.12
, pp. 2726-2736
-
-
Carofiglio, T.1
Cozzi, P.G.2
Floriani, C.3
Chiesa-Villa, A.4
Rizzoli, C.5
-
52
-
-
0037007745
-
-
2/TMSCl-promoted Passerini-type reaction: Xia, Q.; Ganem, B. Org. Lett. 2002, 4, 1631-1634.
-
(2002)
Org. Lett.
, vol.4
, pp. 1631-1634
-
-
Xia, Q.1
Ganem, B.2
-
53
-
-
0346250137
-
-
(b) LiOTf-promoted addition of isocyanides to epoxides and aziridines: Kern, O. T.; Motherwell, W. B. Chem. Commun. 2003, 2988-2989.
-
(2003)
Chem. Commun.
, pp. 2988-2989
-
-
Kern, O.T.1
Motherwell, W.B.2
-
54
-
-
0346025407
-
-
3-mediated addition of isocyanides to epoxides: Bez, G.; Zhao, C.-C. Org. Lett. 2003, 5, 4991-4993.
-
(2003)
Org. Lett.
, vol.5
, pp. 4991-4993
-
-
Bez, G.1
Zhao, C.-C.2
-
55
-
-
0038541773
-
-
3-catalyzed addition of isocyanides to enones: Chatani, N.; Oshita, M.; Tobisu, M.; Ishii, Y.; Murai, Y. J. Am. Chem. Soc. 2003, 125, 7812-7813.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 7812-7813
-
-
Chatani, N.1
Oshita, M.2
Tobisu, M.3
Ishii, Y.4
Murai, Y.5
-
56
-
-
0345376671
-
-
(e) Ti-TADDOL complex promoted Passerini reaction: Kusebauch, U.; Beck, B.; Messer, K.; Herdtweck, E.; Dömling, A. Org. Lett. 2003, 5, 4021-4024.
-
(2003)
Org. Lett.
, vol.5
, pp. 4021-4024
-
-
Kusebauch, U.1
Beck, B.2
Messer, K.3
Herdtweck, E.4
Dömling, A.5
-
58
-
-
0037073229
-
-
(b) Denmark, S. E.; Wynn, T.; Beutner, G. L. J. Am. Chem. Soc. 2002, 124, 13405-13407.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 13405-13407
-
-
Denmark, S.E.1
Wynn, T.2
Beutner, G.L.3
-
61
-
-
11844259698
-
-
Mahrwald, R., Ed.; Wiley-VCH: Weinheim, Chapter 7
-
For full accounts of the development of this concept, see: (a) Denmark, S. E.; Fujimori, S. In Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, 2004; Vol. 2, Chapter 7.
-
(2004)
Modern Aldol Reactions
, vol.2
-
-
Denmark, S.E.1
Fujimori, S.2
-
62
-
-
15744387149
-
-
(b) Denmark, S. E.; Beutner, G. L.; Wynn, T. Eastgate, M. D. J. Am. Chem. Soc. 2005, 127, 3774-3789.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 3774-3789
-
-
Denmark, S.E.1
Beutner, G.L.2
Wynn, T.3
Eastgate, M.D.4
-
64
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Lowering the concentration of the isocyanide may also disfavor the background reaction if the order in isocyanide is higher in this process than in the catalyzed addition. By analogy to other reactions, we expect that the isocyanide is first order in the catalyzed process: (a) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2000, 122, 12021-12022.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 12021-12022
-
-
Denmark, S.E.1
Fu, J.2
-
68
-
-
0037165679
-
-
For the preparation bisphosphoramides 1a-c, see ref 15a; 1d, see ref 18a; 1f, see 18c. For the preparation of bis-N-oxide (P)-(R,R)-1g, see: Denmark, S. E.; Fan, Y. J. Am. Chem. Soc. 2002, 124, 4233-4235.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 4233-4235
-
-
Denmark, S.E.1
Fan, Y.2
-
69
-
-
0037466984
-
-
For a discussion of the origin of the tether length effect, see: Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2003, 125, 2208-2216.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 2208-2216
-
-
Denmark, S.E.1
Fu, J.2
-
70
-
-
0002635992
-
-
(a) Ugi, I.; Meyr, R.; Lipinski, M.; Bodesheim, F.; Rosendahl, F. Org. Synth. 1961, 41, 13-15.
-
(1961)
Org. Synth.
, vol.41
, pp. 13-15
-
-
Ugi, I.1
Meyr, R.2
Lipinski, M.3
Bodesheim, F.4
Rosendahl, F.5
-
71
-
-
0003377834
-
-
Wiley: New York
-
(b) Gokel, G. W.; Widera, R. P.; Weber, W. P. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, pp 232-235.
-
(1988)
Organic Syntheses
, vol.6
, pp. 232-235
-
-
Gokel, G.W.1
Widera, R.P.2
Weber, W.P.3
-
72
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Discussion and Supporting Information
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In the presence of Hünig's base, reaction of 2d with benzaldehyde afforded 8 in 43% yield along with a double addition product 13 in 10% yield. Under these conditions, 2e afforded 9 in 64% yield along with two byproducts, benzoin (14a) in 9% yield and tosylmethylformamide (14b) in 7% yield; see the Discussion and Supporting Information.
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note
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A number of experiments were performed with (S)-1-phenylethyl isocyanide to determine the influence of a chiral isocyanide alone and in double diastereoselection with catalyst (R,R)-1b. In the addition to benzaldehyde, high yields were obtained, but in no case was the influence of the stereogenic center on the isocyanide manifested.
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For the IUPAC definitions of catalyst and pseudocatalyst see http://www.chem.qmul.ac.uk/iupac/gtpoc/.
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note
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The calculations on a complex of benzaldehyde and the dimeric phosphoramide (R,R)-1b bound trichlorosilyl cation were performed using the PC version of GAMESS(US) QC Package employing the PM3 basis set.
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