-
1
-
-
0033529724
-
-
(a) For a comprehensive summary of literature related to the isolation and biological activity of α,β-diamino acids, see: Luo, Y.; Blaskovich, M. A.; Lajoie, G. A. J. Org. Chem. 1999, 64, 6106-6111.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 6106-6111
-
-
Luo, Y.1
Blaskovich, M.A.2
Lajoie, G.A.3
-
2
-
-
0032538362
-
-
(b) Lucet, D.; Gall, T. L.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580-2627.
-
(1998)
Angew. Chem., Int. Ed.
, vol.37
, pp. 2580-2627
-
-
Lucet, D.1
Gall, T.L.2
Mioskowski, C.3
-
4
-
-
0032549502
-
-
For a summary of existing methodology, see ref 1. For recent references, see: (a) Han, H.; Yoon, J.; Janda, K. D. J. Org. Chem. 1998, 63, 2045-2048.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 2045-2048
-
-
Han, H.1
Yoon, J.2
Janda, K.D.3
-
5
-
-
0032555556
-
-
(b) Kuwano, R.; Okuda, S.; Ito, Y. Tetrahedron: Asymmetry 1998, 9, 2773-2775.
-
(1998)
Tetrahedron: Asymmetry
, vol.9
, pp. 2773-2775
-
-
Kuwano, R.1
Okuda, S.2
Ito, Y.3
-
6
-
-
0032570493
-
-
(c) Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1998, 9, 629-646.
-
(1998)
Tetrahedron: Asymmetry
, vol.9
, pp. 629-646
-
-
Merino, P.1
Lanaspa, A.2
Merchan, F.L.3
Tejero, T.4
-
7
-
-
0034807178
-
-
(d) Knudsen, K. R.; Risgaard, T.; Nishiwaki, N.; Gothelf, K. V.; Jørgensen, K. A. J. Am. Chem. Soc. 2001, 123, 5843-5844.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 5843-5844
-
-
Knudsen, K.R.1
Risgaard, T.2
Nishiwaki, N.3
Gothelf, K.V.4
Jørgensen, K.A.5
-
8
-
-
0035902841
-
-
(e) Nishiwaki, N.; Knudsen, K. R.; Gothelf, K. V., Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2992-2995.
-
(2001)
Angew. Chem., Int. Ed.
, vol.40
, pp. 2992-2995
-
-
Nishiwaki, N.1
Knudsen, K.R.2
Gothelf, K.V.3
Jørgensen, K.A.4
-
9
-
-
0033548387
-
-
(f) Zhou, X.-T.; Lin, Y.-R.; Dai, L.-X. Tetrahedron: Asymmetry 1999, 10, 855-862.
-
(1999)
Tetrahedron: Asymmetry
, vol.10
, pp. 855-862
-
-
Zhou, X.-T.1
Lin, Y.-R.2
Dai, L.-X.3
-
12
-
-
0035835947
-
-
See also previous papers by this group. (i) Lee, S. H.; Yoon, J.; Chung, S.-H.; Lee, Y.-S. Tetrahedron 2001, 57, 2139-2145.
-
(2001)
Tetrahedron
, vol.57
, pp. 2139-2145
-
-
Lee, S.H.1
Yoon, J.2
Chung, S.-H.3
Lee, Y.-S.4
-
13
-
-
0035874718
-
-
(j) Robinson, A. J.; Stanislawski, P.; Mulholland, D.; He, L.; Li, H.-Y. J. Org. Chem. 2001, 66, 4148-4152.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 4148-4152
-
-
Robinson, A.J.1
Stanislawski, P.2
Mulholland, D.3
He, L.4
Li, H.-Y.5
-
14
-
-
0041817834
-
-
(k) Pei, W.; Timmons, C.; Xu, X.; Wei, H.-X.; Li, G. Org. Biomol. Chem. 2003, 1, 2919-2921.
-
(2003)
Org. Biomol. Chem.
, vol.1
, pp. 2919-2921
-
-
Pei, W.1
Timmons, C.2
Xu, X.3
Wei, H.-X.4
Li, G.5
-
15
-
-
0036414430
-
-
(l) Ambroise, L.; Dumez, E.; Szeki, A.; Jackson, R. F. W. Synthesis 2002, 2296-2308.
-
(2002)
Synthesis
, pp. 2296-2308
-
-
Ambroise, L.1
Dumez, E.2
Szeki, A.3
Jackson, R.F.W.4
-
16
-
-
0036025621
-
-
(m) Brown, D.; Brown, G. A.; Andrews, M.; Large, J. M.; Urban, D.; Butts, C. P.; Hales, N. J.; Gallagher, T. J. Chem Soc., Perkin Trans. 1 2002, 2014-2021.
-
(2002)
J. Chem Soc., Perkin Trans. 1
, pp. 2014-2021
-
-
Brown, D.1
Brown, G.A.2
Andrews, M.3
Large, J.M.4
Urban, D.5
Butts, C.P.6
Hales, N.J.7
Gallagher, T.8
-
17
-
-
0037077080
-
-
(n) Chhabra, S. R.; Mahajan, A.; Chan, W. C. J. Org. Chem. 2002, 67, 4017-4029.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 4017-4029
-
-
Chhabra, S.R.1
Mahajan, A.2
Chan, W.C.3
-
18
-
-
0026714313
-
-
3: Schmidt, U.; Mundinger, K.; Riedl, B.; Haas, G.; Lau, R. Synthesis 1992, 1201-1202. For a related approach, see: Nakamura, Y.; Hirai, M.; Tamotsu, K.; Yonezawa, Y.; Shin, C. Bull. Chem. Soc. Jpn. 1995, 68, 1369-1377.
-
(1992)
Synthesis
, pp. 1201-1202
-
-
Schmidt, U.1
Mundinger, K.2
Riedl, B.3
Haas, G.4
Lau, R.5
-
19
-
-
0029074988
-
-
3: Schmidt, U.; Mundinger, K.; Riedl, B.; Haas, G.; Lau, R. Synthesis 1992, 1201-1202. For a related approach, see: Nakamura, Y.; Hirai, M.; Tamotsu, K.; Yonezawa, Y.; Shin, C. Bull. Chem. Soc. Jpn. 1995, 68, 1369-1377.
-
(1995)
Bull. Chem. Soc. Jpn.
, vol.68
, pp. 1369-1377
-
-
Nakamura, Y.1
Hirai, M.2
Tamotsu, K.3
Yonezawa, Y.4
Shin, C.5
-
20
-
-
0028296561
-
-
(b) Cleavage of N-carboxyanhydrides derived from β-lactams: Palomo, C.; Aizpurua, J. M.; Cabré, F.; Cuevas, C.; Munt, S.; Odriozola, J. M. Tetrahedron Lett. 1994, 35, 2725-2728. See also: Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Carreaux, F.; Cuevas, C.; Maneiro, E.; Ontoria, J. M. J. Org. Chem. 1994, 59, 3123-3130 See also: Palomo, C.; Aizpurua, J. M.; Galarza, R.; Mielgo, A. Chem. Commun. 1996, 633-634.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 2725-2728
-
-
Palomo, C.1
Aizpurua, J.M.2
Cabré, F.3
Cuevas, C.4
Munt, S.5
Odriozola, J.M.6
-
21
-
-
0000762747
-
-
(b) Cleavage of N-carboxyanhydrides derived from β-lactams: Palomo, C.; Aizpurua, J. M.; Cabré, F.; Cuevas, C.; Munt, S.; Odriozola, J. M. Tetrahedron Lett. 1994, 35, 2725-2728. See also: Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Carreaux, F.; Cuevas, C.; Maneiro, E.; Ontoria, J. M. J. Org. Chem. 1994, 59, 3123-3130 See also: Palomo, C.; Aizpurua, J. M.; Galarza, R.; Mielgo, A. Chem. Commun. 1996, 633-634.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 3123-3130
-
-
Palomo, C.1
Aizpurua, J.M.2
Gamboa, I.3
Carreaux, F.4
Cuevas, C.5
Maneiro, E.6
Ontoria, J.M.7
-
22
-
-
0029877120
-
-
(b) Cleavage of N-carboxyanhydrides derived from β-lactams: Palomo, C.; Aizpurua, J. M.; Cabré, F.; Cuevas, C.; Munt, S.; Odriozola, J. M. Tetrahedron Lett. 1994, 35, 2725-2728. See also: Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Carreaux, F.; Cuevas, C.; Maneiro, E.; Ontoria, J. M. J. Org. Chem. 1994, 59, 3123-3130 See also: Palomo, C.; Aizpurua, J. M.; Galarza, R.; Mielgo, A. Chem. Commun. 1996, 633-634.
-
(1996)
Chem. Commun.
, pp. 633-634
-
-
Palomo, C.1
Aizpurua, J.M.2
Galarza, R.3
Mielgo, A.4
-
23
-
-
0030605917
-
-
(c) From a hydroxyoxazolidinone obtained via Sharpless asymmetric epoxidation: Rossi, E. T.; Yoon, R.; Rosenberg, L.; Meinwald, J. Tetrahedron 1996, 52, 10279-10286.
-
(1996)
Tetrahedron
, vol.52
, pp. 10279-10286
-
-
Rossi, E.T.1
Yoon, R.2
Rosenberg, L.3
Meinwald, J.4
-
24
-
-
0344118919
-
-
(d) From enantiopure β-amino esters by α-hydroxylation and inversion via mesylate: Bunnage, M. E.; Burke, A. J.; Davies, S. G.; Millican, N. L.; Nicholson, R. L.; Roberts, P. M.; Smith, A. D. Org. Biomol. Chem. 2003, 1, 3708-3715.
-
(2003)
Org. Biomol. Chem.
, vol.1
, pp. 3708-3715
-
-
Bunnage, M.E.1
Burke, A.J.2
Davies, S.G.3
Millican, N.L.4
Nicholson, R.L.5
Roberts, P.M.6
Smith, A.D.7
-
25
-
-
1442317042
-
-
note
-
(e) From regioselective ring opening of an aziridine obtained via Sharpless asymmetric aminohydroxylation: see ref 2a.
-
-
-
-
26
-
-
1442292553
-
-
note
-
(f) From (E)-α,β-bis(N-acylamino)acrylates by enantioselective hydrogenation: see ref2b.
-
-
-
-
27
-
-
1442317043
-
-
note
-
(g) From a protected L-serine-derived nitrone by addition of Grignard reagents: see ref 2c.
-
-
-
-
28
-
-
1442267976
-
-
note
-
3: see ref 2i.
-
-
-
-
29
-
-
1442267978
-
-
note
-
(i) From enamides by enantioselective hydrogenation: see ref 2j.
-
-
-
-
30
-
-
0035801908
-
-
(j) From 1,3-dihydro-2-imidazolone by a rather elaborate sequence including resolution: Seo, R.; Ishizuka, T.; Abdel-Aziz, A. A.-M.; Kunieda, T. Tetrahedron Lett. 2001, 42, 6353-6355.
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 6353-6355
-
-
Seo, R.1
Ishizuka, T.2
Abdel-Aziz, A.A.-M.3
Kunieda, T.4
-
31
-
-
0037281853
-
-
(k) Direct diamination of olefins: Muñiz, K.; Nieger, M. Synlett 2003, 211-214.
-
(2003)
Synlett
, pp. 211-214
-
-
Muñiz, K.1
Nieger, M.2
-
32
-
-
0037419152
-
-
(a) For a recent report on the asymmetric Mannich reaction of glycine imino esters, see: Bernardi, L.; Gothelf, A. S.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2003, 68, 2583-2591.
-
(2003)
J. Org. Chem.
, vol.68
, pp. 2583-2591
-
-
Bernardi, L.1
Gothelf, A.S.2
Hazell, R.G.3
Jørgensen, K.A.4
-
33
-
-
0032576810
-
-
(b) For a noteworthy exception, see: Alker, D.; Harwood: L. M.; Williams, C. E. Tetrahedron Lett. 1998, 39, 475-478.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 475-478
-
-
Alker, D.1
Harwood, L.M.2
Williams, C.E.3
-
34
-
-
0000652518
-
-
(c) See also a report describing the oxidative dimerization of lithiated glycinates: Alvarez-Ibarra, C.; Csákÿ, A. G.; Colmenero, B.; Quiroga, M. L. J. Org. Chem. 1997, 62, 2478-2482.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 2478-2482
-
-
Alvarez-Ibarra, C.1
Csákÿ, A.G.2
Colmenero, B.3
Quiroga, M.L.4
-
35
-
-
0030575363
-
-
(d) Hayashi, T.; Kishi, E.; Soloshonok, V. A.; Vozumi, Y. Tetrahedron Lett. 1996, 37, 4969-4972.
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 4969-4972
-
-
Hayashi, T.1
Kishi, E.2
Soloshonok, V.A.3
Vozumi, Y.4
-
36
-
-
0030961675
-
-
(e) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P.; Van Meervelt, L.; Mischenko, N. Tetrahedron Lett. 1997, 38, 4671-4674.
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 4671-4674
-
-
Soloshonok, V.A.1
Avilov, D.V.2
Kukhar, V.P.3
Van Meervelt, L.4
Mischenko, N.5
-
38
-
-
0000030326
-
-
(a) Viso, A.; Fernández de la Pradilla, R.; Guerrero-Strachan, C. ; Alonso, M.; Martínez-Ripoll, M.; André, I. J. Org. Chem. 1997, 62, 2316-2317.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 2316-2317
-
-
Viso, A.1
Fernández De La Pradilla, R.2
Guerrero-Strachan, C.3
Alonso, M.4
Martínez-Ripoll, M.5
André, I.6
-
39
-
-
0038789210
-
-
(b) Viso, A.; Fernández de la Pradilla, R.; García, A.; Guerrero-Strachan, C.; Alonso, M.; Tortosa, M.; Flores, A.; Martí nez-Ripoll, M.; Fonseca, I.; André, I.; Rodriguez, A. Chem.-Eur. J. 2003, 9, 2867-2876.
-
(2003)
Chem.-Eur. J.
, vol.9
, pp. 2867-2876
-
-
Viso, A.1
Fernández De La Pradilla, R.2
García, A.3
Guerrero-Strachan, C.4
Alonso, M.5
Tortosa, M.6
Flores, A.7
Martínez-Ripoll, M.8
Fonseca, I.9
André, I.10
Rodriguez, A.11
-
40
-
-
0345425817
-
-
(c) Viso, A.; Fernández de la Pradilla, R.; García, A.; Alonso, M.; Guerrero-Strachan, C.; Fonseca, I. Synlett 1999, 1543-1545.
-
(1999)
Synlett
, pp. 1543-1545
-
-
Viso, A.1
Fernández De La Pradilla, R.2
García, A.3
Alonso, M.4
Guerrero-Strachan, C.5
Fonseca, I.6
-
42
-
-
0036251138
-
-
(e) Viso, A.; Fernández de la Pradilla, R.; Ló pez-Rodríguez, M. L.; García, A.; Tortosa, M. Synlett 2002, 755-758.
-
(2002)
Synlett
, pp. 755-758
-
-
Viso, A.1
Fernández De La Pradilla, R.2
López-Rodríguez, M.L.3
García, A.4
Tortosa, M.5
-
43
-
-
1442341550
-
-
note
-
A detailed account of these experiments is included in the Supporting Information.
-
-
-
-
44
-
-
1442317044
-
-
note
-
1 = H, Ar = Ph) to p-toluensulfonimine did not render N-tosylimidazolidines related to 1a and 1b but a mixture of racemic N-sulfonyldiamino esters with poor selectivity (syn:anti = 70:30); see ref 5b.
-
-
-
-
46
-
-
1442341553
-
-
note
-
We also reconsidered the use of acidic conditions to hydrolyze imine C; however, addition of different acids to the reaction mixture gave erratic mixtures of imidazolidines and diamino esters probably due to uncontrolled cyclization of the latter with benzaldehyde during the workup process.
-
-
-
-
47
-
-
1442292548
-
-
note
-
For full details of all these experiments, see the Supporting Information.
-
-
-
-
49
-
-
0026000578
-
-
For an isolated example of α-substituted β-unsubstituted derivatives, see: Hartwig, W.; Mittendorf, J. Synthesis 1991, 939-941.
-
(1991)
Synthesis
, pp. 939-941
-
-
Hartwig, W.1
Mittendorf, J.2
-
52
-
-
1442267977
-
-
note
-
2O, rt to reflux or TFA, MeOH, rt to reflux.
-
-
-
-
53
-
-
0038204475
-
-
For a related procedure for the synthesis of piperidines from p-tolylsulfinimines, see: Davis, F. A.; Prasad, K. R.; Nolt, M. B.; Wu, Y. Org. Lett. 2003, 5, 925-927.
-
(2003)
Org. Lett.
, vol.5
, pp. 925-927
-
-
Davis, F.A.1
Prasad, K.R.2
Nolt, M.B.3
Wu, Y.4
-
54
-
-
1442292549
-
-
note
-
2 = Bn), see the Supporting Information.
-
-
-
-
55
-
-
0034697709
-
-
For a recent reference, see: Hulme, A. N.; Montgomery, C. H.; Henderson, D. K. J. Chem. Soc., Perkin Trans. 1 2000, 1837-1841. See also: Reetz, M. T.; Drewes, M. W.; Schwickardi, R. Org. Synth. 1998, 76, 110-122.
-
(2000)
J. Chem. Soc., Perkin Trans. 1
, pp. 1837-1841
-
-
Hulme, A.N.1
Montgomery, C.H.2
Henderson, D.K.3
-
56
-
-
85027967654
-
-
For a recent reference, see: Hulme, A. N.; Montgomery, C. H.; Henderson, D. K. J. Chem. Soc., Perkin Trans. 1 2000, 1837-1841. See also: Reetz, M. T.; Drewes, M. W.; Schwickardi, R. Org. Synth. 1998, 76, 110-122.
-
(1998)
Org. Synth.
, vol.76
, pp. 110-122
-
-
Reetz, M.T.1
Drewes, M.W.2
Schwickardi, R.3
-
57
-
-
1442292552
-
-
note
-
A small amount (<10%) of a tribenzylated derivative, 6c′, was obtained upon dibenzylation of 3c. For full details see the Supporting Information.
-
-
-
-
58
-
-
1442292550
-
-
note
-
1H NMR spectrum.
-
-
-
|