-
1
-
-
23844450692
-
-
For reviews on the synthetic and therapeutic use of nonproteinogenic amino acids, see: a
-
For reviews on the synthetic and therapeutic use of nonproteinogenic amino acids, see: (a) Bridges, R. J.; Esselinger, C. S. Pharmacol. Ther. 2005, 107, 271-285.
-
(2005)
Pharmacol. Ther
, vol.107
, pp. 271-285
-
-
Bridges, R.J.1
Esselinger, C.S.2
-
3
-
-
0037261506
-
-
(c) Johansen. T. N.; Greenwood, J. R.; Frydenvang, K.; Madsen, U.; Krogsgaard-Larsen, P. Chirality 2003, 15, 167-179.
-
(2003)
Chirality
, vol.15
, pp. 167-179
-
-
Johansen, T.N.1
Greenwood, J.R.2
Frydenvang, K.3
Madsen, U.4
Krogsgaard-Larsen, P.5
-
4
-
-
0036269536
-
-
(d) Beck, G. Synlett 2002, 837-850.
-
(2002)
Synlett
, pp. 837-850
-
-
Beck, G.1
-
5
-
-
0036036249
-
-
(e) Nájera, C. Synlett 2002, 1388-1403.
-
(2002)
Synlett
, pp. 1388-1403
-
-
Nájera, C.1
-
7
-
-
0025042488
-
-
Bhide, R.; Mortezaei, R.; Scilimati, A.; Sih, C. J. Tetrahedron Lett. 1990, 31, 4827-4830.
-
(1990)
Tetrahedron Lett
, vol.31
, pp. 4827-4830
-
-
Bhide, R.1
Mortezaei, R.2
Scilimati, A.3
Sih, C.J.4
-
8
-
-
0034699305
-
-
Kawasaki, T.; Enoki, H.; Matsumura, K.; Ohyama, M.; Inagawa, M.; Sakamoto. M. Org. Lett. 2000, 2, 3027-3029.
-
(2000)
Org. Lett
, vol.2
, pp. 3027-3029
-
-
Kawasaki, T.1
Enoki, H.2
Matsumura, K.3
Ohyama, M.4
Inagawa, M.5
Sakamoto, M.6
-
9
-
-
33644521754
-
-
For reviews, see
-
(a) For reviews, see: Pace, J. L.; Yang, G. Biochem. Pharmacol. 2006, 71, 968-980.
-
(2006)
Biochem. Pharmacol
, vol.71
, pp. 968-980
-
-
Pace, J.L.1
Yang, G.2
-
10
-
-
14844340653
-
-
(b) Walker, S.; Chen, L.; Hu, Y.; Rew, Y.; Shin, D.; Boger, D. L. Chem. Rev. 2005, 105, 449-475.
-
(2005)
Chem. Rev
, vol.105
, pp. 449-475
-
-
Walker, S.1
Chen, L.2
Hu, Y.3
Rew, Y.4
Shin, D.5
Boger, D.L.6
-
11
-
-
30744442513
-
-
(c) Welzel, P. Chem. Rev. 2005, 105, 4610-4660.
-
(2005)
Chem. Rev
, vol.105
, pp. 4610-4660
-
-
Welzel, P.1
-
12
-
-
14844339524
-
-
(d) Kahne, D.; Leimkuhler, C.; Lu, W.; Walsh, C. Chem. Rev. 2005, 105, 425-448.
-
(2005)
Chem. Rev
, vol.105
, pp. 425-448
-
-
Kahne, D.1
Leimkuhler, C.2
Lu, W.3
Walsh, C.4
-
16
-
-
32344431531
-
-
(a) Chen, K. X.; Njoroge, F. G.; Arasappan, A.; Venkatraman, S.; Vibulbhan, B.; Yang, W.; Parekh, T. N.; Pichardo, J.; Prongay, A.; Cheng, K. C.; Butkiewicz, N.; Yao, N.; Madison, V.; Girijavallabhan, V. J. Med. Chem. 2006, 49, 995-1005.
-
(2006)
J. Med. Chem
, vol.49
, pp. 995-1005
-
-
Chen, K.X.1
Njoroge, F.G.2
Arasappan, A.3
Venkatraman, S.4
Vibulbhan, B.5
Yang, W.6
Parekh, T.N.7
Pichardo, J.8
Prongay, A.9
Cheng, K.C.10
Butkiewicz, N.11
Yao, N.12
Madison, V.13
Girijavallabhan, V.14
-
18
-
-
0035848567
-
-
(c) Stilz, H. U.; Guba, W.; Jablonka, B.; Just, M.; Klinger, O.; König, W.; Wehner, V.; Zoller, G. J. Med. Chem. 2001, 44, 1158-1176.
-
(2001)
J. Med. Chem
, vol.44
, pp. 1158-1176
-
-
Stilz, H.U.1
Guba, W.2
Jablonka, B.3
Just, M.4
Klinger, O.5
König, W.6
Wehner, V.7
Zoller, G.8
-
22
-
-
33745502124
-
-
(d) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244-1267.
-
(1993)
Angew. Chem., Int. Ed. Engl
, vol.32
, pp. 1244-1267
-
-
Giannis, A.1
Kolter, T.2
-
23
-
-
11244333109
-
-
Over 30 new amino acids have been genetically encoded, see: Wang, L.; Schultz, P. G. Angew. Chem., Int. Ed. 2005, 44, 34-66.
-
Over 30 new amino acids have been genetically encoded, see: Wang, L.; Schultz, P. G. Angew. Chem., Int. Ed. 2005, 44, 34-66.
-
-
-
-
24
-
-
24044496242
-
-
For some reviews, see: a
-
For some reviews, see: (a) Viso, A.; Fernández de la Pradilla, R.; García, A.; Flores, A. Chem. Rev. 2005, 105, 3167-3196.
-
(2005)
Chem. Rev
, vol.105
, pp. 3167-3196
-
-
Viso, A.1
Fernández de la Pradilla, R.2
García, A.3
Flores, A.4
-
26
-
-
4544359931
-
-
(c) Erdik, E. Tetrahedron 2004, 60, 8747-8782.
-
(2004)
Tetrahedron
, vol.60
, pp. 8747-8782
-
-
Erdik, E.1
-
27
-
-
0037244819
-
-
(d) Taggi, A. E.; Hafez, A. M.; Lectka, T. Acc. Chem. Res. 2003, 36, 10-19.
-
(2003)
Acc. Chem. Res
, vol.36
, pp. 10-19
-
-
Taggi, A.E.1
Hafez, A.M.2
Lectka, T.3
-
30
-
-
0038795772
-
-
Asymmetric Synthesis of Novel Sterically Constrained Amino Acids; Symposium-in-Print, Hruby, V. J.; Soloshonok, V. A., Eds. Tetrahedron 2001, 57, 6329-6650 and references cited therein.
-
(h) Asymmetric Synthesis of Novel Sterically Constrained Amino Acids; Symposium-in-Print, Hruby, V. J.; Soloshonok, V. A., Eds. Tetrahedron 2001, 57, 6329-6650 and references cited therein.
-
-
-
-
31
-
-
0041378065
-
-
Gröger, H. Chem. Rev. 2003, 103, 2795-2827.
-
(2003)
Chem. Rev
, vol.103
, pp. 2795-2827
-
-
Gröger, H.1
-
32
-
-
0141570904
-
-
(a) Cekovic, Z. Tetrahedron 2003, 59, 8073-8090.
-
(2003)
Tetrahedron
, vol.59
, pp. 8073-8090
-
-
Cekovic, Z.1
-
33
-
-
0001238367
-
-
Renaud, P, Sibi, M. P, Eds, Wiley-VCH: Weinheim, and references cited therein
-
(b) Feray, L.; Kuznetsov, N.; Renaud, P. In Radicals in Organic Synthesis; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2; pp 246-278 and references cited therein.
-
(2001)
Radicals in Organic Synthesis
, vol.2
, pp. 246-278
-
-
Feray, L.1
Kuznetsov, N.2
Renaud, P.3
-
34
-
-
0037064474
-
-
For a preliminary communication of this work, see
-
For a preliminary communication of this work, see: Boto, A.; Hernández, R.; Montoya, A.; Suárez, E. Tetrahedron Lett. 2002, 43, 8269-8272.
-
(2002)
Tetrahedron Lett
, vol.43
, pp. 8269-8272
-
-
Boto, A.1
Hernández, R.2
Montoya, A.3
Suárez, E.4
-
35
-
-
26444523953
-
-
(a) Boto, A.; Gallardo, J. A.; Hernández, R.; Saavedra, C. J. Tetrahedron Lett. 2005, 46, 7807-7811.
-
(2005)
Tetrahedron Lett
, vol.46
, pp. 7807-7811
-
-
Boto, A.1
Gallardo, J.A.2
Hernández, R.3
Saavedra, C.J.4
-
36
-
-
23944472481
-
-
(b) Boto, A.; De León, Y.; Gallardo, J. A.; Hernández, R. Eur. J. Org. Chem. 2005, 3461-3468.
-
(2005)
Eur. J. Org. Chem
, pp. 3461-3468
-
-
Boto, A.1
De León, Y.2
Gallardo, J.A.3
Hernández, R.4
-
37
-
-
1642578949
-
-
(c) Boto, A.; Hernández, R.; Montoya, A.; Suárez, E. Tetrahedron Lett. 2004, 45, 1559-1563.
-
(2004)
Tetrahedron Lett
, vol.45
, pp. 1559-1563
-
-
Boto, A.1
Hernández, R.2
Montoya, A.3
Suárez, E.4
-
38
-
-
0035900387
-
-
(d) Boto, A.; Hernández, R.; León, Y.; Suárez, E. J. Org. Chem. 2001, 65, 7796-7803.
-
(2001)
J. Org. Chem
, vol.65
, pp. 7796-7803
-
-
Boto, A.1
Hernández, R.2
León, Y.3
Suárez, E.4
-
39
-
-
0343167391
-
-
(e) Boto, A.; Hernández, R.; Suárez, E. J. Org. Chem. 2000, 64, 4930-4937.
-
(2000)
J. Org. Chem
, vol.64
, pp. 4930-4937
-
-
Boto, A.1
Hernández, R.2
Suárez, E.3
-
40
-
-
1842430777
-
-
(a) Maryanoff, B. E.; Zhang, H.-C.; Cohen, J. H.; Turchi, I. J.; Maryanoff, C. A. Chem. Rev. 2004, 104, 1431-1628.
-
(2004)
Chem. Rev
, vol.104
, pp. 1431-1628
-
-
Maryanoff, B.E.1
Zhang, H.-C.2
Cohen, J.H.3
Turchi, I.J.4
Maryanoff, C.A.5
-
41
-
-
0001673091
-
-
Trost, B. M, Fleming, I. Eds, Pergamon Press: Oxford
-
(b) Speckamp, W. N.; Hiemstra, H. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 1047-1082.
-
(1991)
Comprehensive Organic Synthesis
, vol.2
, pp. 1047-1082
-
-
Speckamp, W.N.1
Hiemstra, H.2
-
43
-
-
14944348259
-
-
For the discussion on the reaction mechanism, see
-
For the discussion on the reaction mechanism, see: Boto, A.; Hernández, R.; De León, Y.; Murguía, J. R.; Rodríguez-Afonso, A. Eur. J. Org. Chem. 2005, 673-682.
-
(2005)
Eur. J. Org. Chem
, pp. 673-682
-
-
Boto, A.1
Hernández, R.2
De León, Y.3
Murguía, J.R.4
Rodríguez-Afonso, A.5
-
44
-
-
0000949545
-
-
(a) Ginzel, K. D.; Brungs, P.; Steckhan, E. Tetrahedron 1989, 45, 1691-1701.
-
(1989)
Tetrahedron
, vol.45
, pp. 1691-1701
-
-
Ginzel, K.D.1
Brungs, P.2
Steckhan, E.3
-
47
-
-
0034615536
-
-
(a) Priem, G.; Rocheblave, L.; De Michelis, C.; Courcambeck, J.; Kraus, J. L. J. Chem. Soc. Perkin Trans. 1 2000, 819-824.
-
(2000)
J. Chem. Soc. Perkin Trans. 1
, pp. 819-824
-
-
Priem, G.1
Rocheblave, L.2
De Michelis, C.3
Courcambeck, J.4
Kraus, J.L.5
-
48
-
-
0029871638
-
-
(b) Niddam, V.; Camplo, M.; Le Nguyen, D.; Chermann, J. C.; Kraus, J. L. Bioorg. Med. Chem. Lett. 1996, 6, 609-614.
-
(1996)
Bioorg. Med. Chem. Lett
, vol.6
, pp. 609-614
-
-
Niddam, V.1
Camplo, M.2
Le Nguyen, D.3
Chermann, J.C.4
Kraus, J.L.5
-
49
-
-
0030847825
-
-
(a) Massière, F.; Badet-Denisot, M. A.; René, L.; Badet, B. J. Am. Chem. Soc. 1997, 119, 5748-5749.
-
(1997)
J. Am. Chem. Soc
, vol.119
, pp. 5748-5749
-
-
Massière, F.1
Badet-Denisot, M.A.2
René, L.3
Badet, B.4
-
50
-
-
0036846420
-
-
(b) Yaouancq, L.; Anissimova, M.; Badet-Denisot, M. A.; Badet, B. Eur. J. Org. Chem. 2002, 3573-3579.
-
(2002)
Eur. J. Org. Chem
, pp. 3573-3579
-
-
Yaouancq, L.1
Anissimova, M.2
Badet-Denisot, M.A.3
Badet, B.4
-
52
-
-
0029882693
-
-
(b) Tanaka, K.; Ahn, M.; Watanabe, Y.; Fuji, K. Tetrahedron: Asymmetry 1996, 7, 1771-1782.
-
(1996)
Tetrahedron: Asymmetry
, vol.7
, pp. 1771-1782
-
-
Tanaka, K.1
Ahn, M.2
Watanabe, Y.3
Fuji, K.4
-
53
-
-
0033387458
-
-
For related allyl glycines and their therapeutic uses, see
-
(c) For related allyl glycines and their therapeutic uses, see: Alcón, M.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron: Asymmetry 1999, 10, 4639-4651.
-
(1999)
Tetrahedron: Asymmetry
, vol.10
, pp. 4639-4651
-
-
Alcón, M.1
Moyano, A.2
Pericàs, M.A.3
Riera, A.4
-
55
-
-
0027936717
-
-
Panday, S. K.; Griffart-Brunet, D.; Langlois, N. Tetrahedron Lett. 1994, 35, 6673-6676.
-
(1994)
Tetrahedron Lett
, vol.35
, pp. 6673-6676
-
-
Panday, S.K.1
Griffart-Brunet, D.2
Langlois, N.3
-
56
-
-
27644566248
-
-
(a) Díez, D.; García, P.; Marcos, I. S.; Basabe, P.; Garrido, N. M.; Broughton, H. B.; Urones, J. G. Tetrahedron 2005, 61, 11641-11648.
-
(2005)
Tetrahedron
, vol.61
, pp. 11641-11648
-
-
Díez, D.1
García, P.2
Marcos, I.S.3
Basabe, P.4
Garrido, N.M.5
Broughton, H.B.6
Urones, J.G.7
-
58
-
-
0030592758
-
-
(c) Golubev, A. S.; Sewald, N.; Burger, K. Tetrahedron 1996, 52, 14757-14776.
-
(1996)
Tetrahedron
, vol.52
, pp. 14757-14776
-
-
Golubev, A.S.1
Sewald, N.2
Burger, K.3
-
59
-
-
0001034362
-
-
For a very similar product, see
-
For a very similar product, see: Werner, R. M.; Shokek, O.; Davis, J. T. J. Org. Chem. 1997, 62, 8243-8246.
-
(1997)
J. Org. Chem
, vol.62
, pp. 8243-8246
-
-
Werner, R.M.1
Shokek, O.2
Davis, J.T.3
-
60
-
-
34548724465
-
-
In the NOESY experiment of compound 19, spatial correlations were observed between δH 4.45 (1H, dd, 4-H) and δH 1.92 (3H, s, 2-Me, In the NOESY experiment of compound 18, no correlations between δH 4.41 (1H, dd, 4-H) and δH 1.96 (3H, s, 2-Me) were detected
-
H 1.96 (3H, s, 2-Me) were detected.
-
-
-
-
61
-
-
34548736565
-
-
Theoretical coupling constants were calculated over the minimized structures for both diastereomers, by using the Karplus-Altona equation implemented in the Macromodel 7.0 program. The calculations were performed with an MMFF force field, using high-quality parameters, and repeated with an AMBER force field. Similar results were obtained in both cases
-
(a) Theoretical coupling constants were calculated over the minimized structures for both diastereomers, by using the Karplus-Altona equation implemented in the Macromodel 7.0 program. The calculations were performed with an MMFF force field, using high-quality parameters, and repeated with an AMBER force field. Similar results were obtained in both cases.
-
-
-
-
62
-
-
34548758510
-
-
2,3 = 3.7, 7.3 Hz).
-
2,3 = 3.7, 7.3 Hz).
-
-
-
-
63
-
-
20444483055
-
-
For information on the Karplus-Altona equation, see
-
(c) For information on the Karplus-Altona equation, see: Haasnoot, C. A. G.; de Leeuw, F. A. A. M.; Altona, C. Tetrahedron 1980, 36, 2783-2792.
-
(1980)
Tetrahedron
, vol.36
, pp. 2783-2792
-
-
Haasnoot, C.A.G.1
de Leeuw, F.A.A.M.2
Altona, C.3
-
64
-
-
84986437005
-
-
For more information on this software, see
-
(d) For more information on this software, see: Mohamadi, F.; Richard, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrikson, T.; Stille, W. C. J. Comput. Chem. 1990, 11, 440.
-
(1990)
J. Comput. Chem
, vol.11
, pp. 440
-
-
Mohamadi, F.1
Richard, N.G.J.2
Guida, W.C.3
Liskamp, R.4
Lipton, M.5
Caufield, C.6
Chang, G.7
Hendrikson, T.8
Stille, W.C.9
-
65
-
-
4444226240
-
-
For a review on the subject, see
-
For a review on the subject, see: Couty, F.; Evano, G.; Prim, D. Mini-Rev. Org. Chem. 2004, 1, 133-148.
-
(2004)
Mini-Rev. Org. Chem
, vol.1
, pp. 133-148
-
-
Couty, F.1
Evano, G.2
Prim, D.3
-
66
-
-
0142106416
-
-
Only one example of the synthesis of 4-alkoxyazetidine carboxylic acids has been reported: Akiyama, T.; Daidouji, K.; Fuchibe, K. Org. Lett. 2003, 5, 3691-3693.
-
(a) Only one example of the synthesis of 4-alkoxyazetidine carboxylic acids has been reported: Akiyama, T.; Daidouji, K.; Fuchibe, K. Org. Lett. 2003, 5, 3691-3693.
-
-
-
-
67
-
-
33746255430
-
-
For the preparation of other azetidine carboxylic acids, see:, Int. Ed, and references cited therein
-
(b) For the preparation of other azetidine carboxylic acids, see: Morimoto, H.; Wiedemann, S. H.; Yamaguchi, A.; Harada, S.; Chen, Z.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2006, 45, 3146-3150 and references cited therein.
-
(2006)
Angew. Chem
, vol.45
, pp. 3146-3150
-
-
Morimoto, H.1
Wiedemann, S.H.2
Yamaguchi, A.3
Harada, S.4
Chen, Z.5
Matsunaga, S.6
Shibasaki, M.7
-
70
-
-
0001122927
-
-
(b) Williams, R. M.; Hendrix, J. A. Chem, Rev. 1992, 92, 889-917.
-
(1992)
Chem, Rev
, vol.92
, pp. 889-917
-
-
Williams, R.M.1
Hendrix, J.A.2
-
71
-
-
0000826307
-
-
Bretschneider, T.; Miltz, W.; Münster, P.; Steglich, W. Tetrahedron 1988, 44, 5403-5414.
-
(1988)
Tetrahedron
, vol.44
, pp. 5403-5414
-
-
Bretschneider, T.1
Miltz, W.2
Münster, P.3
Steglich, W.4
-
72
-
-
16044374201
-
-
For related examples, see
-
For related examples, see: Abbenante, G.; Bergman, D. A.; Brinkworth, R. I.; March, D. R.; Reid, R. C.; Hunt, P. A.; James, I. W.; Dancer, R. J.; Garnham, B.; Stoermer, M. L.; Fairlie, D. P. Bioorg. Med. Chem. Lett. 1996, 6, 2531-2536.
-
(1996)
Bioorg. Med. Chem. Lett
, vol.6
, pp. 2531-2536
-
-
Abbenante, G.1
Bergman, D.A.2
Brinkworth, R.I.3
March, D.R.4
Reid, R.C.5
Hunt, P.A.6
James, I.W.7
Dancer, R.J.8
Garnham, B.9
Stoermer, M.L.10
Fairlie, D.P.11
-
73
-
-
0037128493
-
-
(a) Wang, W.; Zhang, J.; Xiong, C.; Hruby, V. J. Tetrahedron Lett. 2002, 43, 2137-2140.
-
(2002)
Tetrahedron Lett
, vol.43
, pp. 2137-2140
-
-
Wang, W.1
Zhang, J.2
Xiong, C.3
Hruby, V.J.4
-
76
-
-
33845278304
-
-
(a) Drueckhammer, D. G.; Barbas, C. F., III; Nozaki, K.; Wong, C.-H.; Wood, C. Y.; Ciufolini, M. A. J. Org. Chem. 1988, 53, 1607-1611.
-
(1988)
J. Org. Chem
, vol.53
, pp. 1607-1611
-
-
Drueckhammer, D.G.1
Barbas III, C.F.2
Nozaki, K.3
Wong, C.-H.4
Wood, C.Y.5
Ciufolini, M.A.6
-
77
-
-
0025238774
-
-
For related furan glycines in anticonvulsivant or sweetening compounds, see
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(b) For related furan glycines in anticonvulsivant or sweetening compounds, see: Kohn, H.; Sawhney, K. N.; LeGall, P.; Conley, J. D.; Robertson, D. W.; Leander, J. D. J. Med. Chem. 1990, 33, 919-926.
-
(1990)
J. Med. Chem
, vol.33
, pp. 919-926
-
-
Kohn, H.1
Sawhney, K.N.2
LeGall, P.3
Conley, J.D.4
Robertson, D.W.5
Leander, J.D.6
-
78
-
-
0025328904
-
-
(c) Janusz, J. M.; Young, P. A.; Blum, R. B.; Riley, C. M. J. Med. Chem. 1990, 33, 1676-1682.
-
(1990)
J. Med. Chem
, vol.33
, pp. 1676-1682
-
-
Janusz, J.M.1
Young, P.A.2
Blum, R.B.3
Riley, C.M.4
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79
-
-
0037013970
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-
For the use of indolyl glycines as synthetic intermediates (dragmacidins and dihydrohamacanthin A synthesis), see: Kawasaki, T.; Ohno, K.; Enoki, H.; Umemoto, Y.; Sakamoto, M. Tetrahedron Lett. 2002, 43, 4245-4248.
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(a) For the use of indolyl glycines as synthetic intermediates (dragmacidins and dihydrohamacanthin A synthesis), see: Kawasaki, T.; Ohno, K.; Enoki, H.; Umemoto, Y.; Sakamoto, M. Tetrahedron Lett. 2002, 43, 4245-4248.
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-
-
-
80
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-
30544439940
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-
For other related compounds, see:, and references cited therein
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(b) For other related compounds, see: Zhao, J. L.; Liu, L.; Zhang, H. B.; Wu, Y. C.; Wang, D.; Chen, Y. J. Synlett 2006, 96-100 and references cited therein.
-
(2006)
Synlett
, pp. 96-100
-
-
Zhao, J.L.1
Liu, L.2
Zhang, H.B.3
Wu, Y.C.4
Wang, D.5
Chen, Y.J.6
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