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Volumn 120, Issue 13, 1998, Pages 3074-3088

Transition-metal aqua complexes of 4,6-dibenzofurandiyl-2,2'-bis(4- phenyloxazoline). Effective catalysis in Diels-Alder reactions showing excellent enantioselectivity, extreme chiral amplification, and high tolerance to water, alcohols, amines, and acids

Author keywords

[No Author keywords available]

Indexed keywords

4,6 DIBENZOFURANDIYL 2,2' BIS(4 PHENYLOXAZOLINE); ACID; ALCOHOL DERIVATIVE; AMINE; COBALT COMPLEX; FERROUS ION; IRON COMPLEX; LIGAND; METAL COMPLEX; PERCHLORATE; UNCLASSIFIED DRUG; WATER; ZINC COMPLEX;

EID: 0032495777     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja973519c     Document Type: Article
Times cited : (221)

References (72)
  • 49
    • 2642602653 scopus 로고    scopus 로고
    • note
    • Thionyl chloride and trifluoroacetic acid are known to produce trifluoroacetyl chloride and then trifluoroacetic anhydride. Therefore, the reactive acylating reagent involved in the present reaction would be the bis mixed anhydride, the bis acid chloride, or mixed types.
  • 50
    • 2642684119 scopus 로고    scopus 로고
    • note
    • 2O, cancels the decrease of enantioselectivity by contamination by an enantioisomeric ligand (see the text).
  • 51
    • 2642696363 scopus 로고    scopus 로고
    • note
    • The authors have deposited atomic coordinates for the structures of (R,R)-1, (R,R)-9, meso-22, and (R,R)-9/(S,S)-9 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained on request from The Director, Cambridge Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, U.K.
  • 52
    • 2642629296 scopus 로고    scopus 로고
    • note
    • The Cambridge Structural Database including 167 797 data (updated in 1997) was used.
  • 54
    • 0000157342 scopus 로고    scopus 로고
    • Examples of magnesium/bisoxazoline complexes: (a) Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1996, 61, 346-355. (b) Cozzi, P. G.; Orioli, P.; Tagliavini, E.; U-Ronchi, A. Tetrahedron Lett. 1997, 38, 145-148.
    • (1996) J. Org. Chem. , vol.61 , pp. 346-355
    • Gothelf, K.V.1    Hazell, R.G.2    Jørgensen, K.A.3
  • 55
    • 0031021997 scopus 로고    scopus 로고
    • Examples of magnesium/bisoxazoline complexes: (a) Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1996, 61, 346-355. (b) Cozzi, P. G.; Orioli, P.; Tagliavini, E.; U-Ronchi, A. Tetrahedron Lett. 1997, 38, 145-148.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 145-148
    • Cozzi, P.G.1    Orioli, P.2    Tagliavini, E.3    U-Ronchi, A.4
  • 56
    • 2642656877 scopus 로고    scopus 로고
    • Strong coordination of triflate ligands to the magnesium ion may be a reason for the poor catalytic activity (see ref 7d)
    • Strong coordination of triflate ligands to the magnesium ion may be a reason for the poor catalytic activity (see ref 7d).
  • 57
    • 2642696362 scopus 로고    scopus 로고
    • note
    • Uncatalyzed Diels-Alder reactions of cyclopentadiene take place at room temperature: 80% of 8a after 5 min with 7a; 7% of 8b after 3 h with 7b.
  • 58
    • 2642656876 scopus 로고    scopus 로고
    • note
    • 16e (32) The structural assignment of A was based on elementary analysis and the FAB-MS spectrum. In the presence of plenty of water under severe conditions, partial hydrolysis of the perchlorate salt of 9 takes place to produce A.
  • 59
    • 2642634342 scopus 로고    scopus 로고
    • note
    • 2 at about 350°C. This heating procedure would produce partly dehydrated nickel species.
  • 60
    • 2642637461 scopus 로고    scopus 로고
    • For the counterion effect in Diels-Alder reactions, see ref 7d
    • For the counterion effect in Diels-Alder reactions, see ref 7d.
  • 61
    • 2642595633 scopus 로고    scopus 로고
    • note
    • 3 (10 mol %): room temperature, 1 h, 93%, endo:exo = 89:11, 0% ee.
  • 62
    • 2642694261 scopus 로고    scopus 로고
    • Unpublished results
    • 2 complex does not undergo dissociation into components even in the presence of 3-acetyl-2-oxazolidine (Kanemasa; S.; Oderaotoshi, Y.; Tanaka, J.; Wada, E. Unpublished results).
    • Kanemasa, S.1    Oderaotoshi, Y.2    Tanaka, J.3    Wada, E.4
  • 63
    • 2642661032 scopus 로고    scopus 로고
    • Unpublished results
    • 2O complex of the 4-substituted isopropylidene-2,2′-bisoxazoline forms these two transition structures depending upon the steric nature of the 4-substituent (Kanemasa, S.; Oderaotoshi, Y.; Adachi, K. Unpublished results).
    • Kanemasa, S.1    Oderaotoshi, Y.2    Adachi, K.3
  • 64
    • 2642667051 scopus 로고    scopus 로고
    • note
    • 2O in the presence of dienophile 7.
  • 65
    • 2642590587 scopus 로고    scopus 로고
    • note
    • The analysis was not completed because of the disorder of the acetone and the perchlorate ions. To solve this problem requires a spherical crystal and correction of absorption.
  • 66
    • 2642684118 scopus 로고    scopus 로고
    • note
    • 2O or under uncatalyzed conditions has been discussed in ref 21.
  • 69
    • 0003775768 scopus 로고
    • Enraf-Nonius: Delft, The Netherlands
    • (a) CAD-4 Software. Version 5. Enraf-Nonius: Delft, The Netherlands, 1989.
    • (1989) CAD-4 Software. Version 5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.