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Volumn 50, Issue 15, 1994, Pages 4363-4384

Enantio- and diastereoselective titanium-TADDOLate catalyzed addition of diethyl and bis(3-buten-1-yl) zinc to aldehydes a full account with preparative details

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL; METAL COMPLEX; TITANIUM COMPLEX; UNCLASSIFIED DRUG;

EID: 0028272208     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)89373-X     Document Type: Article
Times cited : (200)

References (79)
  • 1
    • 0002098511 scopus 로고
    • Katalytische und stöchiometrische enantioselektive Additionen von Diethylzink an Aldehyde mit Hilfe eines neuartigen chiralen Spirotitanats
    • Preliminary communications
    • (1991) Angewandte Chemie , vol.103 , pp. 100-101
    • Schmidt1    Seebach2
  • 3
    • 0000233048 scopus 로고
    • 2,2-Dimethyl-α,α,α′,α′-tetra(naphth-2-yl)-1,3-dioxolan-4,5-dimethanol (DINOL) für die Titanat-vermittelte, enantioselektive Addition von Diethylzink an Aldehyde
    • (1991) Angewandte Chemie , vol.103 , pp. 1383-1385
    • Schimdt1    Seebach2
  • 5
    • 0000389195 scopus 로고
    • On the Mechanisms of Enantioselective Reactions Using ?,?,??,?? -Tetraaryl-1,3-dioxolane-4,5-dimethanol(TADDOL)-Derived Titanates: Differences betweenC2- andC1-symmetrical TADDOLs - facts, implications and generalizations
    • Full paper on the mechanism
    • (1992) Helvetica Chimica Acta , vol.75 , pp. 2171-2209
    • Seebach1    Plattner2    Beck3    Wang4    Hunziker5    Petter6
  • 6
    • 0027396039 scopus 로고
    • For a discussion see, [Tetrahedron-Symposia-in-Print 49 on “Synthesis of Optically Active Compounds - Prospects for the 21st Century”].
    • (1993) Tetrahedron , vol.49 , pp. 1711-1724
    • Seebach1    Hayakawa2    Sakaki3    Schweizer4
  • 7
    • 0001202271 scopus 로고
    • Organische Synthese — wohin?
    • A review article describing our view of the future of organic synthesis see
    • (1990) Angewandte Chemie , vol.102 , pp. 1363-1409
    • Seebach1
  • 9
    • 0001956304 scopus 로고
    • Enantioselektive Addition von Organometallreagentien an Carbonylverbindungen: Übertragung, Vervielfältigung und Verstärkung der Chiralität
    • Review
    • (1991) Angewandte Chemie , vol.103 , pp. 34-55
    • Noyori1    Kitamura2
  • 11
    • 84921168895 scopus 로고
    • Tetrahedron
    • For a general discussion see the introduction in, in print [Tetrahedron-Symposia-in-Print on “Mechanistic Aspects of Polar Organometallic Chemistry”].
    • (1993) Tetrahedron , vol.49
    • Weber1    Seebach2
  • 24
    • 84921147197 scopus 로고    scopus 로고
    • 9
  • 25
    • 84921147196 scopus 로고    scopus 로고
    • Weber, B., hithero unpublished results, ETH Zürich, 1993; see also Scheme 3 in ref.2
  • 26
    • 84921147195 scopus 로고    scopus 로고
    • 4 may be as small as 1 : 200 for high enantioselectivity to be observed!
  • 27
    • 84921147194 scopus 로고    scopus 로고
    • For a complete list of all TADDOLs as of July 1992 see Table 2 in ref.2
  • 29
    • 0002291128 scopus 로고
    • Organometallverbindungen von Titan und Zirconium als selektive nucleophile Reagentien für die Organische Synthese
    • (1983) Angewandte Chemie , vol.95 , pp. 12-26
    • Weidmann1    Seebach2
  • 35
    • 0026619595 scopus 로고
    • The hexaphenyl derivative 1d will be described in a forthcoming paper on the mechanism of Ti-TADDOLate catalyzed Diels-Alder reactions (Marti, R.; Dahinden, R.; Beck, A.K.; Kühnle, F., ETH Zürich), see also
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 1591-1596
    • Irurre1    Alonso-Alija2    Piniella3    Alvarez-Larena4
  • 38
    • 84921147193 scopus 로고    scopus 로고
    • 21.
  • 39
    • 84921147192 scopus 로고    scopus 로고
    • So far, the α-naphthyl-TADDOL was the poorest ligand for the nucleophilic addition to aldehydes described here. ortho-Tolyl- and ortho-methoxyphenyl-TADDOLs have not been tested as yet.
  • 40
    • 84921147191 scopus 로고    scopus 로고
    • 23 above.
  • 41
    • 84921147190 scopus 로고    scopus 로고
    • 2
  • 44
  • 45
    • 84918035465 scopus 로고
    • 3-Brom-3-methyl-2-(trimethylsiloxy)-1-buten – ein neues Cycloadditionsreagens
    • (1979) Angewandte Chemie , vol.91 , pp. 178-259
    • ]Seebach1
  • 47
    • 10344232997 scopus 로고
    • For a very recent review article see, and references cited therein
    • (1993) LC ·GC Int. , vol.6 , pp. 606-610
    • Hinshaw1
  • 54
    • 0002953322 scopus 로고
    • Synthese von Cyclosporin und Analoga: Zusammenhang zwischen Struktur und immunsuppressiver Aktivität
    • (1985) Angewandte Chemie , vol.97 , pp. 88-96
    • Wenger1
  • 57
    • 84921147189 scopus 로고    scopus 로고
    • 32
  • 58
    • 33947332027 scopus 로고
    • According to the old-fashioned but widely used Hanson convention re and si are used irrespective whether the face topicities are reflection-variant or reflection-invariant
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 2731-2742
    • Hanson1
  • 59
    • 37049077643 scopus 로고
    • Nonlinear relationship between the enantioselectivities for asymmetric reactions of monofunctional and bifunctional substrates. Synthesis of practically optically pure diols by the catalytic enantioselective diethylation of terephthalaldehyde
    • Cf. Soai's related work with terephthaldehyde
    • (1992) Journal of the Chemical Society, Chemical Communications , pp. 106-108
    • Soai1    Hori2    Kawahara3
  • 61
    • 84921147188 scopus 로고    scopus 로고
    • 4 to play in the mechanism.
  • 62
    • 84921147187 scopus 로고    scopus 로고
    • 2. The cyclohexyl derivative is now being tested in other types of reactions, and we hope to obtain the crystal structure of this compound. The results will be reported elsewhere. We gratefully acknowledge receipt of a generous sample of the cyclohexyl analog of 1a from Dr. R. O. Duthaler of the Ciba Company (Basel); the compound was prepared by hydrogenation of the TADDOL 1a: Rothe-Streit, P., Duthaler, R. O., Hafner, A. [[Truncated]]
  • 71
    • 84921147186 scopus 로고    scopus 로고
    • Beilsteins Handbuch der Organischen Chemie, 1, E I, 203, E III, 1668.
  • 72
    • 84921147185 scopus 로고    scopus 로고
    • Beilsteins Handbuch der Organischen Chemie, 1, E III, 1746.
  • 73
    • 84921147184 scopus 로고    scopus 로고
    • Beilsteins Handbuch der Organischen Chemie, 6, E III, 108.
  • 74
    • 84921147183 scopus 로고    scopus 로고
    • Beilsteins Handbuch der Organischen Chemie, 6, E II, 504; E III, 1953.
  • 75
    • 84921147182 scopus 로고    scopus 로고
    • a, Beilsteins Handbuch der Organischen Chemie, 6, E III, 2465
  • 77
    • 84921147181 scopus 로고    scopus 로고
    • a, Beilsteins Handbuch der Organischen Chemie, 6, E III, 2465
  • 78
    • 84921147180 scopus 로고    scopus 로고
    • Beilsteins Handbuch der Organischen Chemie, 6, E III, 2741.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.