-
1
-
-
0028757621
-
-
For selected reviews, see: (a) Ugi, I.; Domling, A.; Horl, W. Endeavour 1994, 18, 115-122.
-
(1994)
Endeavour
, vol.18
, pp. 115-122
-
-
Ugi, I.1
Domling, A.2
Horl, W.3
-
2
-
-
0001134412
-
-
(b) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210.
-
(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 3168-3210
-
-
Dömling, A.1
Ugi, I.2
-
9
-
-
17144366282
-
-
(b) Ramon, D. J.; Yus, M. Angew. Chem., Int. Ed. 2005, 44, 1602-1634.
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 1602-1634
-
-
Ramon, D.J.1
Yus, M.2
-
10
-
-
34250862807
-
-
(a) Constable, D. J. C.; Dunn, P. J.; Hayler, J. D.; Humphrey, G. R.; Leazer, J. J. L.; Linderman, R. J.; Lorenz, K.; Manley, J.; Pearlman, B. A.; Wells, A.; Zaks, A.; Zhang, T. Y. Green Chem. 2007, 9, 411-420.
-
(2007)
Green Chem.
, vol.9
, pp. 411-420
-
-
Constable, D.J.C.1
Dunn, P.J.2
Hayler, J.D.3
Humphrey, G.R.4
Leazer, J.J.L.5
Linderman, R.J.6
Lorenz, K.7
Manley, J.8
Pearlman, B.A.9
Wells, A.10
Zaks, A.11
Zhang, T.Y.12
-
11
-
-
17844400030
-
-
(b) Rosamilia, A. E.; Scott, J. L.; Strauss, C. R. Org. Lett. 2005, 7, 1525-1528.
-
(2005)
Org. Lett.
, vol.7
, pp. 1525-1528
-
-
Rosamilia, A.E.1
Scott, J.L.2
Strauss, C.R.3
-
12
-
-
36049036327
-
-
(c) Rosamilia, A. E.; Strauss, C. R.; Scott, J. L. Pure Appl. Chem. 2007, 79, 1869-1877.
-
(2007)
Pure Appl. Chem.
, vol.79
, pp. 1869-1877
-
-
Rosamilia, A.E.1
Strauss, C.R.2
Scott, J.L.3
-
13
-
-
51849100344
-
-
(d) Shi, D. Q.; Ni, S. N.; Yang, F.; Ji, S. J. J. Heterocycl. Chem. 2008, 45, 1275-1280.
-
(2008)
J. Heterocycl. Chem.
, vol.45
, pp. 1275-1280
-
-
Shi, D.Q.1
Ni, S.N.2
Yang, F.3
Ji, S.J.4
-
14
-
-
79953277487
-
-
(e) Andriushchenko, A. Y.; Desenko, S. M.; Chernenko, V. N.; Chebanov, V. A. J. Heterocycl. Chem. 2011, 48, 365-367.
-
(2011)
Heterocycl. Chem.
, vol.48
, pp. 365-367
-
-
Andriushchenko, A.Y.1
Desenko, S.M.2
Chernenko, V.N.3
Chebanov, V.A.J.4
-
15
-
-
0141613585
-
-
For selected electrophilic MCRs, see: Serguchev, Y. A.; PonomarenkoM. V.; Lourie, L. F.; Chernega, A. N. J. Fluorine Chem. 2003, 123, 207-215.
-
(2003)
Fluorine Chem.
, vol.123
, pp. 207-215
-
-
Serguchev, Y.A.1
Ponomarenkom, V.2
Lourie, L.F.3
Chernega, A.N.J.4
-
16
-
-
1642410900
-
-
(b) Nair, V.;Menon, R. S.; Beneesh, P. B.; Sreekumar, V.; Bindu, S. Org. Lett. 2004, 6, 767-769.
-
(2004)
Org. Lett.
, vol.6
, pp. 767-769
-
-
Nair, V.1
Menon, R.S.2
Beneesh, P.B.3
Sreekumar, V.4
Bindu, S.5
-
17
-
-
10044242727
-
-
(c) Nair, V.; Beneesh, P. B.; Sreekumar, V.; Bindu, S.; Menon, R. S.; Deepthi, A. Tetrahedron Lett. 2005, 46, 201-203.
-
(2005)
Tetrahedron Lett.
, vol.46
, pp. 201-203
-
-
Nair, V.1
Beneesh, P.B.2
Sreekumar, V.3
Bindu, S.4
Menon, R.S.5
Deepthi, A.6
-
18
-
-
33746588233
-
-
(d) Yeung, Y. Y.; Gao, X. R.; Corey, E. J. J. Am. Chem. Soc. 2006, 128, 9644-9645.
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 9644-9645
-
-
Yeung, Y.Y.1
Gao, X.R.2
Corey, E.J.3
-
19
-
-
34447125205
-
-
(e) Church, T. L.; Byrne, C. M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2007, 129, 8156-8162.
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 8156-8162
-
-
Church, T.L.1
Byrne, C.M.2
Lobkovsky, E.B.3
Coates, G.W.4
-
20
-
-
44949130811
-
-
(f) Hajra, S.; Bar, S.; Sinha, D.; Maji, B. J. Org. Chem. 2008, 73, 4320-4322.
-
(2008)
J. Org. Chem.
, vol.73
, pp. 4320-4322
-
-
Hajra, S.1
Bar, S.2
Sinha, D.3
Maji, B.4
-
21
-
-
76649105423
-
-
(g) Abe, T.; Takeda, H.; Miwa, Y.; Yamada, K.; Yanada, R.; Ishikura, M. Helv. Chim. Acta 2010, 93, 233-241.
-
(2010)
Helv. Chim. Acta
, vol.93
, pp. 233-241
-
-
Abe, T.1
Takeda, H.2
Miwa, Y.3
Yamada, K.4
Yanada, R.5
Ishikura, M.6
-
22
-
-
64249141431
-
-
(h) Braddock, D. C.; Millan, D. S.; Perez-Fuertes, Y.; Pouwer, R. H.; Sheppard, R. N.; Solanki, S.; White, A. J. P. J. Org. Chem. 2009, 74, 1835-1841.
-
(2009)
J. Org. Chem.
, vol.74
, pp. 1835-1841
-
-
Braddock, D.C.1
Millan, D.S.2
Perez-Fuertes, Y.3
Pouwer, R.H.4
Sheppard, R.N.5
Solanki, S.6
White, A.J.P.7
-
23
-
-
78650891151
-
-
(i) Bonney, K. J.; Braddock, D. C.; White, A. J. P.; Yaqoob, M. J. Org. Chem. 2011, 76, 97-104.
-
(2011)
J. Org. Chem.
, vol.76
, pp. 97-104
-
-
Bonney, K.J.1
Braddock, D.C.2
White, A.J.P.3
Yaqoob, M.4
-
24
-
-
80053540653
-
-
(j) Snyder, S. A.; Treitler, D. S.; Bruchks, A. P.; Sattler, W. J. Am. Chem. Soc. 2011, 133, 15898-15901.
-
(2011)
J. Am. Chem. Soc.
, vol.133
, pp. 15898-15901
-
-
Snyder, S.A.1
Treitler, D.S.2
Bruchks, A.P.3
Sattler, W.4
-
25
-
-
77955018066
-
-
Zhou, L.; Tan, C. K.; Zhou, J.; Yeung, Y.-Y. J. Am. Chem. Soc. 2010, 132, 10245-10247.
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 10245-10247
-
-
Zhou, L.1
Tan, C.K.2
Zhou, J.3
Yeung, Y.-Y.4
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26
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84055221470
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We have briefly investigated using less THF, i.e., using THF as a stoichiometric reagent instead of a solvent. However, the results were not satisfactory. For details, see the Supporting Information
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We have briefly investigated using less THF, i.e., using THF as a stoichiometric reagent instead of a solvent. However, the results were not satisfactory. For details, see the Supporting Information.
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84055187091
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When using salicyclic acid
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When using salicyclic acid
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84055221471
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the corresponding 3,5-dibromosalicyclic adduct was obtained as the sole product. Identical result was observed when using 3,5-diromosalicyclic acid
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(1n), the corresponding 3,5-dibromosalicyclic adduct was obtained as the sole product. Identical result was observed when using 3,5-diromosalicyclic acid
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32
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84055187126
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as the nucleophlic partner
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(o) as the nucleophlic partner.
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33
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84055180988
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4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography to yield the corresponding product
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4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography to yield the corresponding product.
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34
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84055180987
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For the reactions that used acids 11 and 1m (Table 2, entries 11 and 12; Table 3, entries 1 and 2; Table 4), the products existed as diastereoisomeric mixtures
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For the reactions that used acids 11 and 1m (Table 2, entries 11 and 12; Table 3, entries 1 and 2; Table 4), the products existed as diastereoisomeric mixtures.
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35
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84055221468
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The carboxylic acids with neighboring hydroxyl groups (acids 1k, 1l, 1n, and 1o) returned high reaction yields; for acid 1l, removing (Table 2, entry 11 vs 8) or masking (Table 2, entry 11 vs 12) the hydroxyl group gave a lower yield. The hydroxyl group seemed could enhance the acidity of the carboxylic acid, potentially through an intramolecular hydrogen bonding (Table 2, entry 1 vs 13; 8 vs 11
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The carboxylic acids with neighboring hydroxyl groups (acids 1k, 1l, 1n, and 1o) returned high reaction yields; for acid 1l, removing (Table 2, entry 11 vs 8) or masking (Table 2, entry 11 vs 12) the hydroxyl group gave a lower yield. The hydroxyl group seemed could enhance the acidity of the carboxylic acid, potentially through an intramolecular hydrogen bonding (Table 2, entry 1 vs 13; 8 vs 11).
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84055187127
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The details appear in the Supporting Information
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The details appear in the Supporting Information.
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79955603119
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Similar observation appeared in related studies; for reference, see: (a) Zhou, L.; Zhou, J.; Tan, C. K.; Chen, J.; Yeung, Y.-Y. Org. Lett. 2011, 13, 2448-2451.
-
(2011)
Org. Lett
, vol.13
, pp. 2448-2451
-
-
Zhou, L.1
Zhou, J.2
Tan, C.K.3
Chen, J.4
Yeung, Y.-Y.5
-
38
-
-
80055070719
-
-
(b) Zhou, L.; Chen, J.; Zhou, J.; Yeung, Y.-Y. Org. Lett. 2011, 13, 5804-5807.
-
(2011)
Org. Lett.
, vol.13
, pp. 5804-5807
-
-
Zhou, L.1
Chen, J.2
Zhou, J.3
Yeung, Y.-Y.4
-
41
-
-
0001302139
-
-
Patai, S., Ed.; Wiley: New York; Suppl. A, Part 2
-
(c) Schmid, G. H.; Garrat, D. G. In The Chemistry of Double Bonded Functional Groups; Patai, S., Ed.; Wiley: New York, 1977; Suppl. A, Part 2, p 725.
-
(1977)
The Chemistry of Double Bonded Functional Groups
, pp. 725
-
-
Schmid, G.H.1
Garrat, D.G.2
-
42
-
-
79955461496
-
-
(a) Li, Z.; Nakashige, M.; Chain, W. J. J. Am. Chem. Soc. 2011, 133, 6553-6556.
-
(2011)
J. Am. Chem. Soc.
, vol.133
, pp. 6553-6556
-
-
Li, Z.1
Nakashige, M.2
Chain, W.J.3
-
43
-
-
84055166279
-
-
(b) Zhou, Q.; Chen, X.; Ma, D. Angew. Chem., Int. Ed. 2010, 49, 3515-3516.
-
(2010)
Angew. Chem. Int. Ed.
, vol.49
, pp. 3515-3516
-
-
Zhou, Q.1
Chen, X.2
Ma, D.3
-
45
-
-
44949086718
-
-
(b) Chen, K.; Richter, J. M.; Baran, P. S. J. Am. Chem. Soc. 2008, 130, 7247-7249.
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 7247-7249
-
-
Chen, K.1
Richter, J.M.2
Baran, P.S.3
-
47
-
-
33748239489
-
-
(d) Lauer, G.; Oberdorfer, F. Angew. Chem., Int. Ed. 1993, 32, 272-273.
-
(1993)
Angew. Chem., Int. Ed.
, vol.32
, pp. 272-273
-
-
Lauer, G.1
Oberdorfer, F.2
-
48
-
-
80053540653
-
-
For studies of bromonium and related electrophiles activation by Lewis basic sulfur and selenium, see: (a) Synder, S. A.; Treitler,D. S.; Brucks, A. P.; Sattler, W. J. Am. Chem. Soc. 2011, 133, 15898-15901.
-
(2011)
J. Am. Chem. Soc.
, vol.133
, pp. 15898-15901
-
-
Synder, S.A.1
Treitlerd, S.2
Brucks, A.P.3
Sattler, W.4
-
49
-
-
80053311363
-
-
(b) Denmark, S. E.; Kornfilt, D. J. P.; Vogler, T. J. Am. Chem. Soc. 2011, 133, 15308-15311.
-
(2011)
J. Am. Chem. Soc.
, vol.133
, pp. 15308-15311
-
-
Denmark, S.E.1
Kornfilt, D.J.P.2
Vogler, T.3
-
50
-
-
79956160559
-
-
(c) Tan, C. K.; Zhou, L.; Yeung, Y.-Y. Org. Lett. 2011, 13, 2738-2741.
-
(2011)
Org. Lett.
, vol.13
, pp. 2738-2741
-
-
Tan, C.K.1
Zhou, L.2
Yeung, Y.-Y.3
-
51
-
-
79958809866
-
-
(d) Zhou, L.; Chen, J.; Tan, C. K.; Yeung, Y.-Y. J. Am. Chem. Soc. 2011, 133, 9164-9167.
-
(2011)
J. Am. Chem. Soc.
, vol.133
, pp. 9164-9167
-
-
Zhou, L.1
Chen, J.2
Tan, C.K.3
Yeung, Y.-Y.4
-
52
-
-
84860390566
-
-
(e) Tan, C. K.; Chen, F.; Yeung, Y.-Y. Tetrahedron Lett. 2011, 52, 4892-4895.
-
(2011)
Tetrahedron Lett.
, vol.52
, pp. 4892-4895
-
-
Tan, C.K.1
Chen, F.2
Yeung, Y.-Y.3
-
54
-
-
77957719306
-
-
(g) Synder, S. A.; Treitler, D. S.; Brucks, A. P. J. Am. Chem. Soc. 2010, 132, 14303-14314.
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 14303-14314
-
-
Synder, S.A.1
Treitler, D.S.2
Brucks, A.P.3
-
55
-
-
78649736234
-
-
(h) Zhou, L.; Tan, C. K.; Jiang, X.; Chen, F.; Yeung, Y.-Y. J. Am. Chem. Soc. 2010, 132, 15474-15476.
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 15474-15476
-
-
Zhou, L.1
Tan, C.K.2
Jiang, X.3
Chen, F.4
Yeung, Y.-Y.5
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