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Volumn 2, Issue 4, 1996, Pages 382-384

Synthesis, structure, and stereoselective reaction of a chiral hydroxy-stabilized metal-free enolate

Author keywords

Asymmetric synthesis; Chirality; Enolates; Hydrogen bonds; Structure elucidation

Indexed keywords

ASYMMETRIC SYNTHESIS; DIASTEREO-SELECTIVITY; ENOLATES; INTRAMOLECULAR HYDROGEN BONDING; STEREOSELECTIVE REACTIONS; STRUCTURE ELUCIDATION; TETRABUTYLAMMONIUM; TETRABUTYLAMMONIUM HYDROXIDES;

EID: 2042441389     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.19960020405     Document Type: Article
Times cited : (28)

References (44)
  • 3
    • 0000584420 scopus 로고
    • (Ed.: J. D. Morrison), Academic Press, New York
    • b) C. H. Heathcock in Asymmetric Synthesis, Vol. 3 (Ed.: J. D. Morrison), Academic Press, New York, 1984, p. 111;
    • (1984) Asymmetric Synthesis , vol.3 , pp. 111
    • Heathcock, C.H.1
  • 6
    • 0003905731 scopus 로고
    • (Ed.: J. D. Morrison), Academic Press, New York
    • e) D. A. Evans in Asymmetric Synthesis, Vol. 3 (Ed.: J. D. Morrison), Academic Press, New York, 1984;
    • (1984) Asymmetric Synthesis , vol.3
    • Evans, D.A.1
  • 8
  • 9
    • 84891304011 scopus 로고
    • (Ed.: R. Scheffold), Salle + Sauerländer, Frankfurt
    • h) C. H. Heathcock in Modern Synthetic Methods, Vol. 6 (Ed.: R. Scheffold), Salle + Sauerländer, Frankfurt, 1992.
    • (1992) Modern Synthetic Methods , vol.6
    • Heathcock, C.H.1
  • 21
    • 84891328136 scopus 로고    scopus 로고
    • b Ref. [1], p. 364
    • b) Ref. [1], p. 364;
  • 26
    • 21844487312 scopus 로고
    • Related hydrogen bonding between tetraalkylammonium and phosphonium salts of certain nitro and sulfone compounds
    • Related hydrogen bonding between tetraalkylammonium and phosphonium salts of certain nitro and sulfone compounds: a) M. T. Reetz, S. Hütte, R. Goddard, Z. Naturforsch. 1995, 50b, 415;
    • (1995) Z. Naturforsch. , vol.50 B , pp. 415
    • Reetz, M.T.1    Hütte, S.2    Goddard, R.3
  • 30
    • 0001561490 scopus 로고
    • +) as the counterion is monomeric, although the enolate oxygen atom also participates in hydrogen bonds
    • +) as the counterion is monomeric, although the enolate oxygen atom also participates in hydrogen bonds: G. Boche, I. Langlotz, M. Marsch, K. Harms, Chem. Ber. 1994, 127, 2059.
    • (1994) Chem. Ber. , vol.127 , pp. 2059
    • Boche, G.1    Langlotz, I.2    Marsch, M.3    Harms, K.4
  • 34
    • 84891292397 scopus 로고    scopus 로고
    • note
    • -3.
  • 35
    • 33644914006 scopus 로고
    • Examples of hydrogen bonds between "carbanions" and alcohols or water: a 2-Nitrobenzyllithium·EtOH
    • Examples of hydrogen bonds between "carbanions" and alcohols or water: a) 2-Nitrobenzyllithium·EtOH: G. Klebe, K. H. Böhn, M. Marsch, G. Boche, Angew. Chem. 1987, 99, 62;
    • (1987) Angew. Chem. , vol.99 , pp. 62
    • Klebe, G.1    Böhn, K.H.2    Marsch, M.3    Boche, G.4
  • 39
    • 84891336734 scopus 로고    scopus 로고
    • note
    • In all illustrations of the chiral enolate shown in this paper the (S)-configuration is arbitrarily used. Three descriptors are necessary to define the two π faces properly. In the case of the (R)-configurated compound the corresponding two hydrogen bonds to the enolate occur at the Si,Si face.
  • 40
    • 84891341682 scopus 로고    scopus 로고
    • We thank Y. Bautista and G. Boche (Universität Marburg) for providing their apparatus and for assistance in carrying out the cryoscopic measurements
    • We thank Y. Bautista and G. Boche (Universität Marburg) for providing their apparatus and for assistance in carrying out the cryoscopic measurements.
  • 41
    • 84891323531 scopus 로고    scopus 로고
    • note
    • 8]THF solution of a crystalline sample of 4 are more complex than expected and point to the existence of a rapid and reversible retro-aldol process. However, the equilibrium lies far on the side of the enolate 4.
  • 43
    • 0028129220 scopus 로고
    • The question of whether methyl versus phenyl is the determining factor in stereoselective reactions of olefins bearing these groups at the stereogenic allylic position has been discussed for other systems: and references cited therein
    • The question of whether methyl versus phenyl is the determining factor in stereoselective reactions of olefins bearing these groups at the stereogenic allylic position has been discussed for other systems: R. W. Hoffmann, R. Stürmer, K. Harms, Tetrahedron Lett. 1994, 35, 6263, and references cited therein.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 6263
    • Hoffmann, R.W.1    Stürmer, R.2    Harms, K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.