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Volumn 16, Issue 17, 2010, Pages 5036-5042

Solvent-dependent self-discrimination of Bis(2-hydroxyphenyl)diamides

Author keywords

Aggregation; Asymmet ric catalysis; Chiral resolution; Molecular recognition; Self assembly; Stacking interactions

Indexed keywords

ASYMMET-RIC CATALYSIS; CHIRAL RESOLUTIONS; CHLOROMETHANE; DIAMIDES; ETHYL ACETATES; HALOGENATED SOLVENTS; HYDROGEN BONDINGS; PACKING PATTERNS; STACKING INTERACTION;

EID: 77951593664     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201000321     Document Type: Article
Times cited : (26)

References (98)
  • 1
    • 0001384399 scopus 로고
    • For reviews, see: a
    • For reviews, see: a) D. J. Cram, Angew. Chem. 1988, 100, 1041;
    • (1988) Angew. Chem. , vol.100 , pp. 1041
    • Cram, D.J.1
  • 9
    • 0037192455 scopus 로고    scopus 로고
    • c) J.-M. Lehn, Science 2002, 295, 2400;
    • (2002) Science , vol.295 , pp. 2400
    • Lehn, J.-M.1
  • 11
    • 34147181003 scopus 로고    scopus 로고
    • 2nd ed. (Eds.: V. Balzani, A. Credi, M. Venturi), Wiley, New York
    • e) Molecular Devices and Machines, 2nd ed. (Eds.: V. Balzani, A. Credi, M. Venturi), Wiley, New York, 2008.
    • (2008) Molecular Devices and Machines
  • 12
    • 0000633029 scopus 로고    scopus 로고
    • For selected reviews, see: a
    • For selected reviews, see: a) D. Philp, J. F. Stoddart, Angew. Chem. 1996, 108, 1242;
    • (1996) Angew. Chem. , vol.108 , pp. 1242
    • Philp, D.1    Stoddart, J.F.2
  • 38
    • 0040514974 scopus 로고
    • For examples of heterochiral association of metal complexes, see: a
    • For examples of heterochiral association of metal complexes, see: a) M. Kitamura, S. Okada, S. Suga, R. Noyori, J. Am. Chem. Soc. 1989, 111, 4028;
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 4028
    • Kitamura, M.1    Okada, S.2    Suga, S.3    Noyori, R.4
  • 50
    • 34250365737 scopus 로고    scopus 로고
    • For recent reviews on enantioenrichment by crystallization, see: a
    • For recent reviews on enantioenrichment by crystallization, see: a) R. M. Kellogg, Angew. Chem. 2007, 119, 498;
    • (2007) Angew. Chem. , vol.119 , pp. 498
    • Kellogg, R.M.1
  • 63
    • 0036378309 scopus 로고    scopus 로고
    • For other selected examples of asymmetric amplification using dif-fering thermodynamic properties of homochiral and heterochiral ag-gregates, see: a
    • For other selected examples of asymmetric amplification using dif-fering thermodynamic properties of homochiral and heterochiral ag-gregates, see: a) A. Ishii, M. Kanai, K. Higashiyama, K. Mikami, Chirality 2002, 14, 709;
    • (2002) Chirality , vol.14 , pp. 709
    • Ishii, A.1    Kanai, M.2    Higashiyama, K.3    Mikami, K.4
  • 68
  • 83
    • 77951588143 scopus 로고    scopus 로고
    • See the Supporting Information and Experimental Section for de-tails.
    • See the Supporting Information and Experimental Section for de-tails.
  • 84
    • 77951537943 scopus 로고    scopus 로고
    • 2 and AcOEt/n-pentane are provided in the Supporting Information.
    • 2 and AcOEt/n-pentane are provided in the Supporting Information.
  • 85
    • 77951570931 scopus 로고    scopus 로고
    • 3 molecule and proposed that this in-corporation caused a significant enhancement of the eutectic ee value. For a more detailed study on the tuning of eutectic composi-tion by achiral additives, see reference [8e].
    • 3 molecule and proposed that this in-corporation caused a significant enhancement of the eutectic ee value. For a more detailed study on the tuning of eutectic composi-tion by achiral additives, see reference [8e].
  • 86
    • 77951523690 scopus 로고    scopus 로고
    • The amount of (S)-1b, (S)-1c, (S)-1d, (S)-1e, (S)-1 f, and (S)-1g in the filtrate remained almost identical to the initial concentration, whereas the amount of (S)-1a and (R)-1a was significantly de-creased. A small imbalance of the amount of (S)-1a and (R)-1a in the filtered insoluble material indicated that tiny amounts of (R)-1a/ (S)-1b-g aggregates were formed.
    • The amount of (S)-1b, (S)-1c, (S)-1d, (S)-1e, (S)-1 f, and (S)-1g in the filtrate remained almost identical to the initial concentration, whereas the amount of (S)-1a and (R)-1a was significantly de-creased. A small imbalance of the amount of (S)-1a and (R)-1a in the filtered insoluble material indicated that tiny amounts of (R)-1a/ (S)-1b-g aggregates were formed.
  • 87
    • 77951524223 scopus 로고    scopus 로고
    • Similar experiments were performed previously, see references [8b] and [9].
    • Similar experiments were performed previously, see references [8b] and [9].
  • 88
    • 37349005457 scopus 로고    scopus 로고
    • For recent reviews on direct Mannich reactions using unmodified pronucleophiles, see: a For general reviews on catalytic asymmetric Mannich re-actions, see
    • For recent reviews on direct Mannich reactions using unmodified pronucleophiles, see: a) A. Ting, S. E. Schaus, Eur. J. Org. Chem. 2007, 5797. For general reviews on catalytic asymmetric Mannich re-actions, see:
    • (2007) Eur. J. Org. Chem. , pp. 5797
    • Ting, A.1    Schaus, S.E.2
  • 89
    • 10844266525 scopus 로고    scopus 로고
    • (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Spring-er, Berlin, Chapter 295
    • b) S. Kobayashi, M. Ueno in Comprehensive Asymmet-ric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Spring-er, Berlin, 2003, Chapter 295, p. 143;
    • (2003) Comprehensive Asymmet-ric Catalysis , pp. 143
    • Kobayashi, S.1    Ueno, M.2
  • 93
    • 0043028789 scopus 로고    scopus 로고
    • For recent reviews for electrophilic amination of carbonyl com-pounds, see: a
    • For recent reviews for electrophilic amination of carbonyl com-pounds, see: a) R.O. Duthaler, Angew. Chem. 2003, 115, 1005;
    • (2003) Angew. Chem. , vol.115 , pp. 1005
    • Duthaler, R.O.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.