-
1
-
-
0019163001
-
-
(a) Freidinger, R. M.; Veber, D. F.; Perlow, D. S.; Brookas, J. R.; Saperstein, R. Science 1980, 210, 656-658.
-
(1980)
Science
, vol.210
, pp. 656-658
-
-
Freidinger, R.M.1
Veber, D.F.2
Perlow, D.S.3
Brookas, J.R.4
Saperstein, R.5
-
3
-
-
0035959447
-
-
For reviews, see: a
-
For reviews, see: (a) Souers, A. J.; Ellman, J. A. Tetrahedron 2001, 57, 7431-7448.
-
(2001)
Tetrahedron
, vol.57
, pp. 7431-7448
-
-
Souers, A.J.1
Ellman, J.A.2
-
4
-
-
0030768259
-
-
(b) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854.
-
(1997)
Tetrahedron
, vol.53
, pp. 12789-12854
-
-
Hanessian, S.1
McNaughton-Smith, G.2
Lombart, H.-G.3
Lubell, W.D.4
-
5
-
-
10044292363
-
Synthesis of Peptides Incorporating β-Turn Inducers and Mimetics
-
Goodman, M, Felix, A, Moroder, L, Toniolo, C, Eds, Thieme: Stuttgart, New York, and references therein
-
(c) Kahn, M.; Eguchi, M. Synthesis of Peptides Incorporating β-Turn Inducers and Mimetics. In Houben-Weyl, Methods of Organic Chemistry; Goodman, M., Felix, A., Moroder, L., Toniolo, C., Eds.; Thieme: Stuttgart, New York, 2003; Vol. E22c, pp 695-740 and references therein.
-
(2003)
Houben-Weyl, Methods of Organic Chemistry
, vol.E22c
, pp. 695-740
-
-
Kahn, M.1
Eguchi, M.2
-
6
-
-
0003461218
-
-
Lehn, J.-M, Atwood, J. L, Davies, J. E. D, MacNicol, D. D, Vögtle, F, Eds, Pergamon: Oxford
-
Comprehensive Supramolecular Chemistry; Lehn, J.-M., Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Pergamon: Oxford, 1996.
-
(1996)
Comprehensive Supramolecular Chemistry
-
-
-
7
-
-
9144267831
-
-
Palomo, C.; Aizpurua, J. M.; Benito, A.; Miranda, J. I.; Fratila, R. M.; Matute, C.; Domercq, M.; Gago, F.; Martin-Santamaria, S.; Linden, A. J. Am. Chem. Soc. 2003, 125, 16243-16260.
-
(2003)
J. Am. Chem. Soc
, vol.125
, pp. 16243-16260
-
-
Palomo, C.1
Aizpurua, J.M.2
Benito, A.3
Miranda, J.I.4
Fratila, R.M.5
Matute, C.6
Domercq, M.7
Gago, F.8
Martin-Santamaria, S.9
Linden, A.10
-
8
-
-
33749176923
-
-
(a) Macias, A.; Ramallal, A. M.; Alonso, E.; Del Pozo, C.; Gonzalez, J. J. Org. Chem. 2006, 71, 7721-7730.
-
(2006)
J. Org. Chem
, vol.71
, pp. 7721-7730
-
-
Macias, A.1
Ramallal, A.M.2
Alonso, E.3
Del Pozo, C.4
Gonzalez, J.5
-
9
-
-
0033581577
-
-
(b) Palomo, C.; Aizpurua, J. M.; Benito, A.; Galarza, R.; Khamrai, U. K.; Vazquez, J.; DePascual-Teresa, B.; Nieto, P. M.; Linden, A. Angew. Chem., Int. Ed. 1999, 38, 3056-3058.
-
(1999)
Angew. Chem., Int. Ed
, vol.38
, pp. 3056-3058
-
-
Palomo, C.1
Aizpurua, J.M.2
Benito, A.3
Galarza, R.4
Khamrai, U.K.5
Vazquez, J.6
DePascual-Teresa, B.7
Nieto, P.M.8
Linden, A.9
-
10
-
-
0029874671
-
-
(c) Wu, Z.; Georg, G. I.; Cathers, B. E.; Schloss, J. V. Bioorg. Med. Chem. Lett. 1996, 6, 983-986.
-
(1996)
Bioorg. Med. Chem. Lett
, vol.6
, pp. 983-986
-
-
Wu, Z.1
Georg, G.I.2
Cathers, B.E.3
Schloss, J.V.4
-
11
-
-
0034751733
-
-
1 = H): (a) Turner, J. J.; Sikkema, F. D.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Synlett 2001, 1727-1730.
-
1 = H): (a) Turner, J. J.; Sikkema, F. D.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Synlett 2001, 1727-1730.
-
-
-
-
12
-
-
0027512269
-
-
(b) Sreenivasan, U.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1993, 36, 256-263.
-
(1993)
J. Med. Chem
, vol.36
, pp. 256-263
-
-
Sreenivasan, U.1
Mishra, R.K.2
Johnson, R.L.3
-
13
-
-
10044262066
-
-
For related β-substituted β-lactam scaffolds, see: c
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For related β-substituted β-lactam scaffolds , see: (c) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Benito, A.; Cuerdo, L.; Fratila, R. M.; Jimenez, A.; Loinaz, I.; Miranda, J. I.; Pytlewska, K. R.; Micle, A.; Linden, A. Org. Lett. 2004, 6, 4443-4446.
-
(2004)
Org. Lett
, vol.6
, pp. 4443-4446
-
-
Palomo, C.1
Aizpurua, J.M.2
Ganboa, I.3
Benito, A.4
Cuerdo, L.5
Fratila, R.M.6
Jimenez, A.7
Loinaz, I.8
Miranda, J.I.9
Pytlewska, K.R.10
Micle, A.11
Linden, A.12
-
14
-
-
0035929452
-
-
(d) Alonso, E.; López-Ortiz, F.; Del Pozo, C.; Peralta, E.; Macías, A.; González, J. J. Org. Chem. 2001, 66, 6333-6338.
-
(2001)
J. Org. Chem
, vol.66
, pp. 6333-6338
-
-
Alonso, E.1
López-Ortiz, F.2
Del Pozo, C.3
Peralta, E.4
Macías, A.5
González, J.6
-
17
-
-
25144488663
-
-
Broadrup, R. L.; Wang, B.; Malachowski, W. P. Tetrahedron 2005, 61, 10277-10284.
-
(2005)
Tetrahedron
, vol.61
, pp. 10277-10284
-
-
Broadrup, R.L.1
Wang, B.2
Malachowski, W.P.3
-
19
-
-
33748299109
-
-
(b) Bittermann, H.; Böckler, F.; Einsiedel, J.; Gmeiner, P. Chem. - Eur. J. 2006, 12, 6315-6322.
-
(2006)
Chem. - Eur. J
, vol.12
, pp. 6315-6322
-
-
Bittermann, H.1
Böckler, F.2
Einsiedel, J.3
Gmeiner, P.4
-
20
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33846457075
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2 = H, R = Bn) under several Mitsunobu conditions, including those reported in refs 7 and 8.
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2 = H, R = Bn) under several Mitsunobu conditions, including those reported in refs 7 and 8.
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21
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33846403428
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Alternative access to β-N-peptidyl-azaserinates 9 was also explored from α-amino esters (including unhindered benzyl glycinate) and α-substituted serines with the hydroxy group activated as O-mesylate 13 and lactone 14, but all attempts to prepare the desired α,β-diamino esters met with failure. (Chemical Equation Presented)
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Alternative access to β-N-peptidyl-azaserinates 9 was also explored from α-amino esters (including unhindered benzyl glycinate) and α-substituted serines with the hydroxy group activated as O-mesylate 13 and lactone 14, but all attempts to prepare the desired α,β-diamino esters met with failure. (Chemical Equation Presented)
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22
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33748605775
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Monographs on the reactivity of aziridines: (a) Tanner, D
-
Monographs on the reactivity of aziridines: (a) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599-619.
-
(1994)
Angew. Chem., Int. Ed. Engl
, vol.33
, pp. 599-619
-
-
-
23
-
-
0002054640
-
-
Padwa, A, Ed, Pergamon: New York
-
(b) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Pergamon: New York, 1996; Vol. 1A, p 1-60.
-
(1996)
Comprehensive Heterocyclic Chemistry II
, vol.1 A
, pp. 1-60
-
-
Pearson, W.H.1
Lian, B.W.2
Bergmeier, S.C.3
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26
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84987557280
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Available from (D)-serine. See: Seebach, D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194-1216.
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Available from (D)-serine. See: Seebach, D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194-1216.
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27
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3342925158
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For a related one-pot tosylation/aziridination of α,β- aminoalcohols, see
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For a related one-pot tosylation/aziridination of α,β- aminoalcohols, see: Bieber, L. W.; de Araujo, M. C. F. Molecules 2002, 7, 902-906.
-
(2002)
Molecules
, vol.7
, pp. 902-906
-
-
Bieber, L.W.1
de Araujo, M.C.F.2
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28
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17844401298
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To the best of our knowledge, these examples represent the first general preparation of α-substituted β-N-peptidyl-azaserines in enantiopure form. For stereocontrolled synthesis of α-substituted β-N-alkyl-azaserines, see: (a) Pfammatter, E.; Seebach, D. Liebigs Ann. Chem. 1991, 1323-1336.
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To the best of our knowledge, these examples represent the first general preparation of α-substituted β-N-peptidyl-azaserines in enantiopure form. For stereocontrolled synthesis of α-substituted β-N-alkyl-azaserines, see: (a) Pfammatter, E.; Seebach, D. Liebigs Ann. Chem. 1991, 1323-1336.
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-
-
-
29
-
-
0030607173
-
-
(b) Burgaud, B. G. M.; Horwell, D. C.; Padova, A.; Pritchard, M. C. Tetrahedron 1996, 52, 13035-13050.
-
(1996)
Tetrahedron
, vol.52
, pp. 13035-13050
-
-
Burgaud, B.G.M.1
Horwell, D.C.2
Padova, A.3
Pritchard, M.C.4
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30
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33846450743
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For a related carboxylic acid-amine cyclization on α-unsubstituted β-N-peptidyl azaserines, see ref 6a
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For a related carboxylic acid-amine cyclization on α-unsubstituted β-N-peptidyl azaserines, see ref 6a.
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-
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31
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33846437166
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A survey of procedures to obtain 2-azetidinones by cyclization of β-amino esters:, Müller, E, Bayer, O, Eds, Thieme: Stuttgart
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A survey of procedures to obtain 2-azetidinones by cyclization of β-amino esters: Backes, J. In Houben-Weyl, Methoden der Organischen Chemie, Band E16b: Müller, E., Bayer, O., Eds.; Thieme: Stuttgart, 1991; pp 97-101.
-
(1991)
Houben-Weyl, Methoden der Organischen Chemie, Band E16b
, pp. 97-101
-
-
Backes, J.1
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32
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33846449975
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β-Aminoalcohol tert-butyldimethylsilyl ethers 26 were prepared in 75-95% overall yields from the corresponding α-amino acids. See Supporting Information for details.
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β-Aminoalcohol tert-butyldimethylsilyl ethers 26 were prepared in 75-95% overall yields from the corresponding α-amino acids. See Supporting Information for details.
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-
33
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0023089147
-
-
Gennari, C.; Venturini, I.; Gilson, G.; Schimperna, G. Tetrahedron Lett. 1987, 28, 227-230.
-
(1987)
Tetrahedron Lett
, vol.28
, pp. 227-230
-
-
Gennari, C.1
Venturini, I.2
Gilson, G.3
Schimperna, G.4
-
34
-
-
0037940081
-
-
De Luca, L.; Giacomelli, G.; Masala, S.; Porcheddu, A. J. Org. Chem. 2003, 68, 4999-5001.
-
(2003)
J. Org. Chem
, vol.68
, pp. 4999-5001
-
-
De Luca, L.1
Giacomelli, G.2
Masala, S.3
Porcheddu, A.4
-
35
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30044437894
-
-
For some reviews on the preparation of α,α-disubstituted amino esters, see: a
-
For some reviews on the preparation of α,α-disubstituted amino esters, see: (a) Ohfune, Y.; Shinada, T. Eur. J. Org. Chem. 2005, 5127-5143.
-
(2005)
Eur. J. Org. Chem
, pp. 5127-5143
-
-
Ohfune, Y.1
Shinada, T.2
-
38
-
-
33846464269
-
-
(b) Kiso, Y.; Kai, Y.; Yajima, H. Chem. Pharm. Bull. 1973, 21, 2570-2510.
-
(1973)
Chem. Pharm. Bull
, vol.21
, pp. 2570-2510
-
-
Kiso, Y.1
Kai, Y.2
Yajima, H.3
-
39
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33846408753
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3N (water-soluble carbodiimide method), complete epimerization was observed at the α′ position.
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3N ("water-soluble carbodiimide method"), complete epimerization was observed at the α′ position.
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40
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0030790051
-
-
Maligres, P. E.; See, M. M.; Askin, D.; Reider, P. J. Tetrahedron Lett. 1997, 38, 5253-5256.
-
(1997)
Tetrahedron Lett
, vol.38
, pp. 5253-5256
-
-
Maligres, P.E.1
See, M.M.2
Askin, D.3
Reider, P.J.4
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