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For example, see Cragg, G. M., Kingston, D. G. I., Newman, D. J., Eds.; CRC Press: Boca Raton, FL
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For example, see: Gueritte, F.; Fahy, J. In Anticancer Agents from Natural Products; Cragg, G. M., Kingston, D. G. I., Newman, D. J., Eds.; CRC Press: Boca Raton, FL, 2005; pp 123-135.
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Gueritte, F.1
Fahy, J.2
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2
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0034728665
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For leading references to drug candidates that bear a 2-methylindoline subunit, see: Nicolaou, K. C.; Roecker, A. J.; Pfefferkorn, J. A.; Cao, G.-Q. J. Am. Chem. Soc. 2000, 122, 2966-2967.
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Nicolaou, K.C.1
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Cao, G.-Q.4
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3
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0034625892
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For example, see: (a) Ruthenium-catalyzed hydrogenation of N-protected indoles: Kuwano, R.; Sato, K.; Kurokawa, T.; Karube, D.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 7614-7615.
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Ito, Y.5
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33645913553
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Kuwano, R.; Kashiwabara, M.; Sato, K.; Ito, T.; Kaneda, K.; Ito, Y. Tetrahedron: Asymmetry 2006, 17, 521-535.
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Kuwano, R.1
Kashiwabara, M.2
Sato, K.3
Ito, T.4
Kaneda, K.5
Ito, Y.6
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6
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33644933443
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(b) Palladium-catalyzed cyclization of N-acyl anilines: Yip, K.-T.; Yang, M.; Law, K.-L.; Zhu, N.-Y.; Yang, D. J. Am. Chem. Soc. 2006, 128, 3130-3131.
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Yip, K.-T.1
Yang, M.2
Law, K.-L.3
Zhu, N.-Y.4
Yang, D.5
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7
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2642560480
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(c) Enzyme-catalyzed hydrolysis of racemic N-Boc-indoline-2-carboxylic esters: Kurokawa, M.; Sugai, T. Bull. Chem. Soc. Jpn. 2004, 77, 1021-1025.
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Bull. Chem. Soc. Jpn.
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Kurokawa, M.1
Sugai, T.2
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8
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85050296727
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For reviews, see: (a) Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249-330.
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Fiaud, J.C.2
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0002178750
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(b) Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 1, 5-26.
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Keith, J.M.1
Larrow, J.F.2
Jacobsen, E.N.3
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11
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21344465658
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(d) Vedejs, E.; Jure, M. Angew. Chem., Int. Ed. 2005, 44, 3974-4001.
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Vedejs, E.1
Jure, M.2
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0346199337
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For examples and leading references, see
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For examples and leading references, see: van Rantwijk, F.; Sheldon, R. A. Tetrahedron 2004, 60, 501-519.
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Tetrahedron
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Van Rantwijk, F.1
Sheldon, R.A.2
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13
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0035825126
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Arai, S.; Bellemin-Laponnaz, S.; Fu, G. C. Angew. Chem., Int. Ed. 2001, 40, 234-236.
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Arai, S.1
Bellemin-Laponnaz, S.2
Fu, G.C.3
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33646737239
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Birman, V. B.; Jiang, H.; Li, X.; Guo, L.; Uffman, E. W. J. Am. Chem. Soc. 2006, 128, 6536-6537.
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Birman, V.B.1
Jiang, H.2
Li, X.3
Guo, L.4
Uffman, E.W.5
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15
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33750718255
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note
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A preliminary study suggests that, when catalyst 2 is N-acetylated, it is a poor electrophile for an indoline.
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-
-
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16
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33750738656
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note
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In the absence of a catalyst, <1% acetylation is observed.
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17
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0035900958
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Tao, B.; Lo, M. M.-C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 353-354.
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J. Am. Chem. Soc.
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Tao, B.1
Lo, M.M.-C.2
Fu, G.C.3
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18
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0034665237
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5H) can be synthesized from Ar-Br in a single step: Dyker, G.; Heiermann, J.; Miura, M.; Inoh, J.-I.; Pivsa-Art, S.; Satoh, T.; Nomura, M. Chem.-Eur. J. 2000, 6, 3426-3433.
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Chem.-Eur. J.
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Dyker, G.1
Heiermann, J.2
Miura, M.3
Inoh, J.-I.4
Pivsa-Art, S.5
Satoh, T.6
Nomura, M.7
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19
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0033921576
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For a discussion of catalyst design, see: Fu, G. C. Acc. Chem. Res. 2000, 33, 412-420.
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Acc. Chem. Res.
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Fu, G.C.1
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20
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0034695460
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For an earlier study of kinetic resolutions of 1-phenylethylamine by such stoichiometric chiral acylating agents, see: Ie, Y.; Fu, G. C. Chem. Commun. 2000, 119-120.
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Chem. Commun.
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Ie, Y.1
Fu, G.C.2
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21
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18244398432
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3-NMeCl) for N-acetylations of racemic 1-phenylethylamine by a stoichiometric chiral acylating agent: Arseniyadis, S.; Subhash, P. V.; Valleix, A.; Mathew, S. P.; Blackmond, D. G.; Wagner, A.; Mioskowski, C. J. Am. Chem. Soc. 2005, 127, 6138-6139.
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Arseniyadis, S.1
Subhash, P.V.2
Valleix, A.3
Mathew, S.P.4
Blackmond, D.G.5
Wagner, A.6
Mioskowski, C.7
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22
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23044443893
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University Science Books: Sausalito, CA
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a values for various crown ethers and alkali-metal cations, see: Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic Chemistry; University Science Books: Sausalito, CA, 2006; p 227.
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Modern Physical Organic Chemistry
, pp. 227
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Anslyn, E.V.1
Dougherty, D.A.2
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23
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1542582866
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See also
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See also: Izatt, R. M.; Pawlak, K.; Bradshaw, J. S. Chem. Rev. 1991, 91, 1721-2085.
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(1991)
Chem. Rev.
, vol.91
, pp. 1721-2085
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Izatt, R.M.1
Pawlak, K.2
Bradshaw, J.S.3
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24
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33750689943
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note
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Clearly, long reaction times are not ideal. On the other hand, this kinetic-resolution method avoids protection/deprotection of the indole, which is necessary for the most general alternative approach to the catalytic synthesis of enantionriched indolines (ref 3a).
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25
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33750693787
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note
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2-hybridized, low selectivity is observed.
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26
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33750743495
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note
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(a) However, an indoline that bears two electronegative fluorine substituents (4,5-difluoro-2-methylindoline) reacts very slowly and with moderate selectivity (s ≈ 7).
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27
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33750688293
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note
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(b) Catalyst 1 can be recovered in good yield (> 80%).
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28
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33750687624
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note
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We have been able to achieve the kinetic resolution of a 2-substituted pyrrolidine with s ≈ 4. To the best of our knowledge, this is the first example of a kinetic resolution of a dialkylamine with promising selectivity by a nonenzymatic acylation catalyst.
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29
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0040292267
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Preliminary studies of the dependence of the selectivity factor on the catalyst ee provide no evidence for the presence of species that contain more than one catalyst molecule. (a) Johnson, D. W., Jr.; Singleton, D. A. J. Am. Chem. Soc. 1999, 121, 9307-9312.
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(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 9307-9312
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Johnson Jr., D.W.1
Singleton, D.A.2
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30
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0000906552
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Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, Chapter 4.1
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(b) Kagan, H. B.; Luukas, T. O. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Chapter 4.1.
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(1999)
Comprehensive Asymmetric Catalysis
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Kagan, H.B.1
Luukas, T.O.2
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31
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33750710190
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note
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This may be a consequence of the enhanced acidity of the N-bound proton of an indoline, relative to a primary benzylic amine.
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