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36349033298
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85077848655
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From the reduction of α-amino ketones: a
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Tramontini, M.1
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(b) Hoffman, R. V.; Maslouh, N.; Cervantes-Lee, F. J. Org. Chem. 2002, 67, 1045.
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Fraser, D.S.1
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84970571837
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From the manipulation of cyanohydrins: d
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From the manipulation of cyanohydrins: (d) Jackson, W. R.; Jacobs, H. A.; Jayatilake, G. S.; Matthews, B. R.; Watson, K. G. Aust. J. Chem. 1990, 43, 2045.
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Watson, K.G.5
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19
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33745424910
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From nucleophilic additions to α-amino aldehydes: e
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From nucleophilic additions to α-amino aldehydes: (e) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531.
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Reetz, M.T.1
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20
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0035966177
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From nucleophilic additions to chiral imine derivatives: f
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From nucleophilic additions to chiral imine derivatives: (f) Tang, T. P.; Volkman, S. K.; Ellman, J. A. J. Org. Chem. 2001, 66, 8772.
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Tang, T.P.1
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21
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0035843416
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(g) Barrow, J. C.; Ngo, P. L.; Pellicore, J. M.; Selnick, H. G.; Nantermet, P. G. Tetrahedron Lett. 2001, 42, 2051.
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Barrow, J.C.1
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22
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33646462433
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From the reduction of nitrogen-stabilized oxallyl cation [4+3] cycloadducts: (h) Huang, J.; Ianni, J. C.; Antoline, J. E.; Hsung, R. P.; Kozlowski, M. C. Org. Lett. 2006, 8, 1565.
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From the reduction of nitrogen-stabilized oxallyl cation [4+3] cycloadducts: (h) Huang, J.; Ianni, J. C.; Antoline, J. E.; Hsung, R. P.; Kozlowski, M. C. Org. Lett. 2006, 8, 1565.
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84945057233
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0343203021
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(c) Prasad, B.; Saund, A. K.; Bora, J. M.; Mathur, N. K. Ind. J. Chem. 1974, 12, 290.
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(h) Dharanipragada, R.; Alarcon, A.; Hruby, V. J. Org. Prep. Proced. Int. 1991, 23, 396.
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(a) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361.
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Hodgson, D.M.1
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Lee, G.P.3
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34
-
-
67749090407
-
-
Comprehensive Organic Synthesis, Part 1.3.4.1., 6; Mitsunobu, O.; Winterfeldt, E., Eds.; Pergamon: New York, 1996.
-
(b) Comprehensive Organic Synthesis, Part 1.3.4.1., Vol. 6; Mitsunobu, O.; Winterfeldt, E., Eds.; Pergamon: New York, 1996.
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35
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0038468227
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(c) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
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Chem. Rev
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Ager, D.J.1
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-
37
-
-
67749098970
-
-
Cost per gram from Aldrich Chemical Company: ethyl (2S)-lactate: £0.05; (2S)-2-methyloxirane: £8.66.
-
Cost per gram from Aldrich Chemical Company: ethyl (2S)-lactate: £0.05; (2S)-2-methyloxirane: £8.66.
-
-
-
-
40
-
-
33947468007
-
-
(c) Shapiro, S. L.; Rose, I. M.; Freedman, L. J. Am. Chem. Soc. 1959, 81, 6322.
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(1959)
J. Am. Chem. Soc
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, pp. 6322
-
-
Shapiro, S.L.1
Rose, I.M.2
Freedman, L.3
-
42
-
-
67749143171
-
-
4: (a) See ref. 13d.
-
4: (a) See ref. 13d.
-
-
-
-
43
-
-
0042249054
-
-
(b) Yoneyama, K.; Ichizen, N.; Konnai, M.; Takematsu, T.; Ushinohama, K.; Jikihara, T. Agric. Biol. Chem. 1984, 48, 995.
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Agric. Biol. Chem
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, pp. 995
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-
Yoneyama, K.1
Ichizen, N.2
Konnai, M.3
Takematsu, T.4
Ushinohama, K.5
Jikihara, T.6
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44
-
-
0027493557
-
-
(c) Lai, J.-Y.; Shi, X.-X.; Gong, Y.-S.; Dai, L.-X. J. Org. Chem. 1993, 58, 4775.
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J. Org. Chem
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, pp. 4775
-
-
Lai, J.-Y.1
Shi, X.-X.2
Gong, Y.-S.3
Dai, L.-X.4
-
45
-
-
67749139064
-
-
4: (d) Taoka, N, Yasohara, Y, Yao, T, Maehara, K, Ueda, Y. WO 2002070482, 2002
-
4: (d) Taoka, N.; Yasohara, Y.; Yao, T.; Maehara, K.; Ueda, Y. WO 2002070482, 2002.
-
-
-
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48
-
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33845553090
-
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(b) Brown, H. C.; Choi, Y. M.; Narasimhan, S. J. Org. Chem. 1982, 47, 3153.
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J. Org. Chem
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, pp. 3153
-
-
Brown, H.C.1
Choi, Y.M.2
Narasimhan, S.3
-
49
-
-
67749085548
-
-
Synthesis of Lactamides 8a-n, General Procedure Ethyl (2S)-lactate (7, 88.2 mmol, 1 equiv) and the appropriate amine (114.6 mmol, 1.3 equiv) were placed in a flask and heated under reflux for 24 h. The solution was allowed to cool to r.t, the volatiles were removed under reduced pressure (1.33·10-4 bar, and the lactamide was purified by vacuum distillation or recrystallization. For the synthesis of bislactamides 8k and 8l, 0.5 equiv of amine were used. Compounds 8a-d,f-j,l-n are known.20 Characterization Data for 8e Yellow oil, bp 101-104°C (1.33·10-4 bar, α] D16 -16.6 (c 1.31, CHCl3, IR (neat, 3308 (OH, NH, 2978, 1655 (C=O, 1532, 1457, 1364, 1275, 1124, 1048, 978 cm -1. 1H NMR (400.1 MHz, CDCl3, δ, 6.90 (s, 1 H, exch. D2O, NH, 4.18 (q, J, 6.5 Hz, 1 H, CHOH, 3.84 b
-
+: 227.1008; found: 227.1010.
-
-
-
-
50
-
-
67749146553
-
-
Synthesis of β-Amino Alcohols 9a-n, General Procedure The lactamide 8 (23.7 mmol, 1 equiv) was dissolved in dry 1,2-dimethoxyethane (15 mL/g) in an oven-dried flask equipped with a Dean-Stark trap and reflux condenser under a nitrogen atmosphere. Boron trifluoride etherate (47.5 mmol, 2 equiv) was added, and then borane-methyl sulfide (47.5 mmol, 2 equiv) was added dropwise via syringe. Once the evolution of H2 had ceased, the solution was heated under reflux for 24 h (ca. 2-3 mL of distillate collected) and the solvents were removed in vacuo. The resulting colorless oil was carefully diluted with 6 M HCl (15 mL/g) and boiled for ca. 5 min. The resulting clear solution was neutralized while still hot with 6 M NaOH (15 mL/g) and then allowed to cool to r.t. before being saturated with solid K2CO3 and extracted with CHCl3 3 x 50 mL, The combined organic extracts were dried over MgSO4 and evaporated to afford the crude β-amino al
-
2)
-
-
-
-
51
-
-
33748786287
-
-
Lactamides 8a-d have recently been used as chiral auxiliaries, see: Ammazzalorso, A.; Amoroso, R.; Bettoni, G.; De Filippis, B.; Fantacuzzi, M.; Giampietro, L.; Maccallini, C.; Tricca, M. L. Eur. J. Org. Chem. 2006, 4088.
-
Lactamides 8a-d have recently been used as chiral auxiliaries, see: Ammazzalorso, A.; Amoroso, R.; Bettoni, G.; De Filippis, B.; Fantacuzzi, M.; Giampietro, L.; Maccallini, C.; Tricca, M. L. Eur. J. Org. Chem. 2006, 4088.
-
-
-
-
52
-
-
67749145019
-
-
Compound 8a: (a) See ref. 13a.
-
Compound 8a: (a) See ref. 13a.
-
-
-
-
53
-
-
0024463710
-
-
(b) Ito, Y.; Kobayashi, Y.; Kawabata, T.; Takase, M.; Terashima, S. Tetrahedron 1989, 45, 5767.
-
(1989)
Tetrahedron
, vol.45
, pp. 5767
-
-
Ito, Y.1
Kobayashi, Y.2
Kawabata, T.3
Takase, M.4
Terashima, S.5
-
55
-
-
67749130239
-
-
See ref. 13a
-
(d) See ref. 13a.
-
-
-
-
56
-
-
0002526211
-
-
(e) Schurig, V.; Hintzer, K.; Leyrer, U.; Mark, C.; Pitchen, P.; Kagan, H. B. J. Organomet. Chem. 1989, 370, 81.
-
(1989)
J. Organomet. Chem
, vol.370
, pp. 81
-
-
Schurig, V.1
Hintzer, K.2
Leyrer, U.3
Mark, C.4
Pitchen, P.5
Kagan, H.B.6
-
57
-
-
67749109433
-
-
See ref. 20c
-
(f) See ref. 20c.
-
-
-
-
58
-
-
67749128698
-
-
Compound 8c: (g) See ref. 13a.
-
Compound 8c: (g) See ref. 13a.
-
-
-
-
59
-
-
0027183990
-
-
(h) Tasaka, A.; Tamura, N.; Matsushita, Y.; Teranishi, K.; Hayashi, R. Chem. Pharm. Bull. 1993, 41, 1035.
-
(1993)
Chem. Pharm. Bull
, vol.41
, pp. 1035
-
-
Tasaka, A.1
Tamura, N.2
Matsushita, Y.3
Teranishi, K.4
Hayashi, R.5
-
60
-
-
1842787547
-
-
(i) Upadhayaya, R.-S.; Sinha, N.; Jain, S.; Kishore, N.; Chandra, R.; Arora, S.-K. Bioorg. Med. Chem. 2004, 12, 2225.
-
(2004)
Bioorg. Med. Chem
, vol.12
, pp. 2225
-
-
Upadhayaya, R.-S.1
Sinha, N.2
Jain, S.3
Kishore, N.4
Chandra, R.5
Arora, S.-K.6
-
61
-
-
67749112814
-
-
Compound 8d: (j) See ref. 19.
-
Compound 8d: (j) See ref. 19.
-
-
-
-
62
-
-
67749134862
-
-
Racemic 8f: (k) See ref 13a,c
-
Racemic 8f: (k) See ref 13a,c.
-
-
-
-
63
-
-
0030793169
-
-
Compound 8g: (l) Adamczyk, M.; Grote, J.; Rege, S. Tetrahedron: Asymmetry 1997, 8, 2509.
-
Compound 8g: (l) Adamczyk, M.; Grote, J.; Rege, S. Tetrahedron: Asymmetry 1997, 8, 2509.
-
-
-
-
64
-
-
0037007715
-
-
Compound 8h: (m) Savinov, S. N.; Austin, D. J. Org. Lett. 2002, 4, 1415.
-
Compound 8h: (m) Savinov, S. N.; Austin, D. J. Org. Lett. 2002, 4, 1415.
-
-
-
-
65
-
-
67749115613
-
-
Compound 8i: (n) See ref. 14c.
-
Compound 8i: (n) See ref. 14c.
-
-
-
-
66
-
-
0000945454
-
-
Compound 8j: (o) Harada, K.; Munegumi, T.; Nomoto, S. Tetrahedron Lett. 1981, 22, 111.
-
Compound 8j: (o) Harada, K.; Munegumi, T.; Nomoto, S. Tetrahedron Lett. 1981, 22, 111.
-
-
-
-
68
-
-
67749109432
-
-
See ref. 14c
-
(q) See ref. 14c.
-
-
-
-
69
-
-
67749119279
-
Compound 8l: (r) Kern, T
-
Compound 8l: (r) Kern, T. Makromol. Chem. 1955, 16, 89.
-
(1955)
Makromol. Chem
, vol.16
, pp. 89
-
-
-
70
-
-
4243163152
-
-
Compound 8m: (s) Tounsi, N.; Dupont, L.; Mohamadou, A.; Cadiou, C.; Aplincourt, M.; Plantier-Royon, R.; Massicot, F.; Portella, C. New J. Chem. 2004, 28, 785.
-
Compound 8m: (s) Tounsi, N.; Dupont, L.; Mohamadou, A.; Cadiou, C.; Aplincourt, M.; Plantier-Royon, R.; Massicot, F.; Portella, C. New J. Chem. 2004, 28, 785.
-
-
-
-
71
-
-
67749098969
-
-
Compound 8n: (t) See ref. 20s.
-
Compound 8n: (t) See ref. 20s.
-
-
-
-
72
-
-
22144473995
-
-
Racemic 9a: (a) Reid, W. B.; Wright, J. B. Jr.; Kolloff, H. G.; Hunter, J. H. J. Am. Chem. Soc. 1948, 70, 3100.
-
Racemic 9a: (a) Reid, W. B.; Wright, J. B. Jr.; Kolloff, H. G.; Hunter, J. H. J. Am. Chem. Soc. 1948, 70, 3100.
-
-
-
-
73
-
-
0012045447
-
-
(b) Halverstadt, I. F.; Hardie, W. R.; Williams, A. R. J. Am. Chem. Soc. 1959, 81, 3618.
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(1959)
J. Am. Chem. Soc
, vol.81
, pp. 3618
-
-
Halverstadt, I.F.1
Hardie, W.R.2
Williams, A.R.3
-
75
-
-
18844473871
-
-
Compound 9b: (d) Rojkovicova, T.; Lehotay, J.; Cizmarik, J. Pharmazie 2003, 58, 483.
-
Compound 9b: (d) Rojkovicova, T.; Lehotay, J.; Cizmarik, J. Pharmazie 2003, 58, 483.
-
-
-
-
76
-
-
21044443212
-
-
(e) Martin-Matute, B.; Edin, M.; Bogar, K.; Kaynak, F. B.; Baeckvall, J.-E. J. Am. Chem. Soc. 2005, 127, 8817.
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(2005)
J. Am. Chem. Soc
, vol.127
, pp. 8817
-
-
Martin-Matute, B.1
Edin, M.2
Bogar, K.3
Kaynak, F.B.4
Baeckvall, J.-E.5
-
77
-
-
0000012340
-
Compound 9c: (f) Angeloni, A. S
-
Compound 9c: (f) Angeloni, A. S. Gazz. Chim. Ital. 1977, 107, 421.
-
(1977)
Gazz. Chim. Ital
, vol.107
, pp. 421
-
-
-
78
-
-
67749109431
-
Racemic 9d: (g) Redel, B
-
Racemic 9d: (g) Redel, B. Bull. Soc. Chim. Fr. 1955, 92, 1411.
-
(1955)
Bull. Soc. Chim. Fr
, vol.92
, pp. 1411
-
-
-
79
-
-
84984088781
-
-
(h) Bourquin, J.-P.; Schwarb, G.; Gamboni, G.; Fischer, R.; Ruesch, L.; Guldimann, S.; Theus, V.; Schenker, E.; Renz, J. Helv. Chim. Acta 1958, 41, 1072.
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(1958)
Helv. Chim. Acta
, vol.41
, pp. 1072
-
-
Bourquin, J.-P.1
Schwarb, G.2
Gamboni, G.3
Fischer, R.4
Ruesch, L.5
Guldimann, S.6
Theus, V.7
Schenker, E.8
Renz, J.9
-
80
-
-
0014386959
-
Racemic 9g: (i) Beckett, M
-
Racemic 9g: (i) Beckett, M. J. Pharm. Pharmacol. 1968, 20, 218.
-
(1968)
J. Pharm. Pharmacol
, vol.20
, pp. 218
-
-
-
81
-
-
37049082063
-
-
Compound 9h: (j) Kashima, C.; Harada, K. J. Chem. Soc., Perkin Trans. 1 1988, 1521.
-
Compound 9h: (j) Kashima, C.; Harada, K. J. Chem. Soc., Perkin Trans. 1 1988, 1521.
-
-
-
-
82
-
-
0035902412
-
-
(k) Brun, E. M.; Gil, S.; Parra, M. Tetrahedron: Asymmetry 2001, 12, 915.
-
(2001)
Tetrahedron: Asymmetry
, vol.12
, pp. 915
-
-
Brun, E.M.1
Gil, S.2
Parra, M.3
-
83
-
-
0037621620
-
-
(l) Gawronski, J.; Kolbon, H.; Kwit, M. Enantiomer 2002, 7, 85 .
-
(2002)
Enantiomer
, vol.7
, pp. 85
-
-
Gawronski, J.1
Kolbon, H.2
Kwit, M.3
-
84
-
-
67749085549
-
-
Compound 9i: (m) See ref. 14b.
-
Compound 9i: (m) See ref. 14b.
-
-
-
-
85
-
-
67749130237
-
-
See ref. 14c
-
(n) See ref. 14c.
-
-
-
-
86
-
-
67749098968
-
-
Compound 9j: (o) See ref. 14b.
-
Compound 9j: (o) See ref. 14b.
-
-
-
-
87
-
-
67749139063
-
-
See ref. 14c
-
(p) See ref. 14c.
-
-
-
-
88
-
-
0000908098
-
-
Racemic 9k: (q) Steck, E. A.; Buck, J. S.; Fletcher, L. T. J. Am. Chem. Soc. 1957, 79, 4414.
-
Racemic 9k: (q) Steck, E. A.; Buck, J. S.; Fletcher, L. T. J. Am. Chem. Soc. 1957, 79, 4414.
-
-
-
-
89
-
-
0000502437
-
-
(r) Hall, J. L.; Dean, W. E.; Pacovsky, E. A. J. Am. Chem. Soc. 1960, 82, 3303.
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(1960)
J. Am. Chem. Soc
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Hall, J.L.1
Dean, W.E.2
Pacovsky, E.A.3
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