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Volumn 128, Issue 44, 2006, Pages 14264-14265

Kinetic resolutions of lndolines by a nonenzymatic acylation catalyst

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYLINDOLINE; 2 OXAZOLIDINONE DERIVATIVE; AMINE; INDOLE DERIVATIVE; INDOLINE DERIVATIVE; UNCLASSIFIED DRUG; INDOLINE;

EID: 33750685325     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0657859     Document Type: Article
Times cited : (157)

References (31)
  • 1
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    • For example, see Cragg, G. M., Kingston, D. G. I., Newman, D. J., Eds.; CRC Press: Boca Raton, FL
    • 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.
    • (2005) Anticancer Agents from Natural Products , pp. 123-135
    • Gueritte, F.1    Fahy, J.2
  • 7
    • 2642560480 scopus 로고    scopus 로고
    • (c) Enzyme-catalyzed hydrolysis of racemic N-Boc-indoline-2-carboxylic esters: Kurokawa, M.; Sugai, T. Bull. Chem. Soc. Jpn. 2004, 77, 1021-1025.
    • (2004) Bull. Chem. Soc. Jpn. , vol.77 , pp. 1021-1025
    • Kurokawa, M.1    Sugai, T.2
  • 12
    • 0346199337 scopus 로고    scopus 로고
    • For examples and leading references, see
    • For examples and leading references, see: van Rantwijk, F.; Sheldon, R. A. Tetrahedron 2004, 60, 501-519.
    • (2004) Tetrahedron , vol.60 , pp. 501-519
    • Van Rantwijk, F.1    Sheldon, R.A.2
  • 15
    • 33750718255 scopus 로고    scopus 로고
    • note
    • A preliminary study suggests that, when catalyst 2 is N-acetylated, it is a poor electrophile for an indoline.
  • 16
    • 33750738656 scopus 로고    scopus 로고
    • note
    • In the absence of a catalyst, <1% acetylation is observed.
  • 19
    • 0033921576 scopus 로고    scopus 로고
    • For a discussion of catalyst design, see: Fu, G. C. Acc. Chem. Res. 2000, 33, 412-420.
    • (2000) Acc. Chem. Res. , vol.33 , pp. 412-420
    • Fu, G.C.1
  • 20
    • 0034695460 scopus 로고    scopus 로고
    • 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.
    • (2000) Chem. Commun. , pp. 119-120
    • Ie, Y.1    Fu, G.C.2
  • 22
    • 23044443893 scopus 로고    scopus 로고
    • University Science Books: Sausalito, CA
    • 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.
    • (2006) Modern Physical Organic Chemistry , pp. 227
    • Anslyn, E.V.1    Dougherty, D.A.2
  • 24
    • 33750689943 scopus 로고    scopus 로고
    • note
    • 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).
  • 25
    • 33750693787 scopus 로고    scopus 로고
    • note
    • 2-hybridized, low selectivity is observed.
  • 26
    • 33750743495 scopus 로고    scopus 로고
    • note
    • (a) However, an indoline that bears two electronegative fluorine substituents (4,5-difluoro-2-methylindoline) reacts very slowly and with moderate selectivity (s ≈ 7).
  • 27
    • 33750688293 scopus 로고    scopus 로고
    • note
    • (b) Catalyst 1 can be recovered in good yield (> 80%).
  • 28
    • 33750687624 scopus 로고    scopus 로고
    • note
    • 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.
  • 29
    • 0040292267 scopus 로고    scopus 로고
    • 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.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 9307-9312
    • Johnson Jr., D.W.1    Singleton, D.A.2
  • 30
    • 0000906552 scopus 로고    scopus 로고
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, Chapter 4.1
    • (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.
    • (1999) Comprehensive Asymmetric Catalysis
    • Kagan, H.B.1    Luukas, T.O.2
  • 31
    • 33750710190 scopus 로고    scopus 로고
    • note
    • This may be a consequence of the enhanced acidity of the N-bound proton of an indoline, relative to a primary benzylic amine.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.