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Volumn 58, Issue 41, 2002, Pages 8307-8312

Activation of ether functionality of allyl vinyl ethers by chiral bis(organoaluminum) Lewis acids: Application to asymmetric Claisen rearrangement

Author keywords

Carbonyl compounds; Chiral Lewis acids; Claisen rearrangement

Indexed keywords

ALUMINUM DERIVATIVE; LEWIS ACID; VINYL DERIVATIVE;

EID: 0037037897     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00981-X     Document Type: Article
Times cited : (27)

References (26)
  • 1
    • 0002564128 scopus 로고
    • Reviews: (a) Bartlett P.A. Tetrahedron. 36:1980;3 (b) Gajewski J.J. Hydrocarbon Thermal Isomerizations. 1981;Academic, New York, (c) Lutz R.P. Chem. Rev. 84:1984;205 (d) Hill R.K. Morrison J.D., Asymmetric Synthesis. Vol. 3:1984;503 Academic, New York, (e) Murray A.W. Org. React. Mech. 1986;429 Murray A.W. Org. React. Mech. 1987;457 (f) Moody C.J. Adv. Heterocycl. Chem. 42:1987;203 (g) Ziegler F.E. Chem. Rev. 88:1988;1423 (h) Kallmerten J., Wittman M.D. Stud. Nat. Prod. Chem. 3:1989;233 (i) Blechert S. Synthesis. 1989;71 (j) Wipf P. Trost B.M., Fleming I., Paquette L.A., Comprehensive Organic Synthesis. Vol. 5:1991;827. Chapter 7.2.
    • (1980) Tetrahedron , vol.36 , pp. 3
    • Bartlett, P.A.1
  • 2
    • 0004266297 scopus 로고
    • Academic New York
    • Reviews: (a) Bartlett P.A. Tetrahedron. 36:1980;3 (b) Gajewski J.J. Hydrocarbon Thermal Isomerizations. 1981;Academic, New York, (c) Lutz R.P. Chem. Rev. 84:1984;205 (d) Hill R.K. Morrison J.D., Asymmetric Synthesis. Vol. 3:1984;503 Academic, New York, (e) Murray A.W. Org. React. Mech. 1986;429 Murray A.W. Org. React. Mech. 1987;457 (f) Moody C.J. Adv. Heterocycl. Chem. 42:1987;203 (g) Ziegler F.E. Chem. Rev. 88:1988;1423 (h) Kallmerten J., Wittman M.D. Stud. Nat. Prod. Chem. 3:1989;233 (i) Blechert S. Synthesis. 1989;71 (j) Wipf P. Trost B.M., Fleming I., Paquette L.A., Comprehensive Organic Synthesis. Vol. 5:1991;827. Chapter 7.2.
    • (1981) Hydrocarbon Thermal Isomerizations
    • Gajewski, J.J.1
  • 3
    • 33845471185 scopus 로고
    • Reviews: (a) Bartlett P.A. Tetrahedron. 36:1980;3 (b) Gajewski J.J. Hydrocarbon Thermal Isomerizations. 1981;Academic, New York, (c) Lutz R.P. Chem. Rev. 84:1984;205 (d) Hill R.K. Morrison J.D., Asymmetric Synthesis. Vol. 3:1984;503 Academic, New York, (e) Murray A.W. Org. React. Mech. 1986;429 Murray A.W. Org. React. Mech. 1987;457 (f) Moody C.J. Adv. Heterocycl. Chem. 42:1987;203 (g) Ziegler F.E. Chem. Rev. 88:1988;1423 (h) Kallmerten J., Wittman M.D. Stud. Nat. Prod. Chem. 3:1989;233 (i) Blechert S. Synthesis. 1989;71 (j) Wipf P. Trost B.M., Fleming I., Paquette L.A., Comprehensive Organic Synthesis. Vol. 5:1991;827. Chapter 7.2.
    • (1984) Chem. Rev. , vol.84 , pp. 205
    • Lutz, R.P.1
  • 4
    • 0000639923 scopus 로고
    • J.D. Morrison. Academic New York
    • Reviews: (a) Bartlett P.A. Tetrahedron. 36:1980;3 (b) Gajewski J.J. Hydrocarbon Thermal Isomerizations. 1981;Academic, New York, (c) Lutz R.P. Chem. Rev. 84:1984;205 (d) Hill R.K. Morrison J.D., Asymmetric Synthesis. Vol. 3:1984;503 Academic, New York, (e) Murray A.W. Org. React. Mech. 1986;429 Murray A.W. Org. React. Mech. 1987;457 (f) Moody C.J. Adv. Heterocycl. Chem. 42:1987;203 (g) Ziegler F.E. Chem. Rev. 88:1988;1423 (h) Kallmerten J., Wittman M.D. Stud. Nat. Prod. Chem. 3:1989;233 (i) Blechert S. Synthesis. 1989;71 (j) Wipf P. Trost B.M., Fleming I., Paquette L.A., Comprehensive Organic Synthesis. Vol. 5:1991;827. Chapter 7.2.
    • (1984) Asymmetric Synthesis , vol.3 , pp. 503
    • Hill, R.K.1
  • 5
    • 0004199295 scopus 로고
    • Reviews: (a) Bartlett P.A. Tetrahedron. 36:1980;3 (b) Gajewski J.J. Hydrocarbon Thermal Isomerizations. 1981;Academic, New York, (c) Lutz R.P. Chem. Rev. 84:1984;205 (d) Hill R.K. Morrison J.D., Asymmetric Synthesis. Vol. 3:1984;503 Academic, New York, (e) Murray A.W. Org. React. Mech. 1986;429 Murray A.W. Org. React. Mech. 1987;457 (f) Moody C.J. Adv. Heterocycl. Chem. 42:1987;203 (g) Ziegler F.E. Chem. Rev. 88:1988;1423 (h) Kallmerten J., Wittman M.D. Stud. Nat. Prod. Chem. 3:1989;233 (i) Blechert S. Synthesis. 1989;71 (j) Wipf P. Trost B.M., Fleming I., Paquette L.A., Comprehensive Organic Synthesis. Vol. 5:1991;827. Chapter 7.2.
    • (1986) Org. React. Mech. , pp. 429
    • Murray, A.W.1
  • 6
    • 0004199297 scopus 로고
    • Reviews: (a) Bartlett P.A. Tetrahedron. 36:1980;3 (b) Gajewski J.J. Hydrocarbon Thermal Isomerizations. 1981;Academic, New York, (c) Lutz R.P. Chem. Rev. 84:1984;205 (d) Hill R.K. Morrison J.D., Asymmetric Synthesis. Vol. 3:1984;503 Academic, New York, (e) Murray A.W. Org. React. Mech. 1986;429 Murray A.W. Org. React. Mech. 1987;457 (f) Moody C.J. Adv. Heterocycl. Chem. 42:1987;203 (g) Ziegler F.E. Chem. Rev. 88:1988;1423 (h) Kallmerten J., Wittman M.D. Stud. Nat. Prod. Chem. 3:1989;233 (i) Blechert S. Synthesis. 1989;71 (j) Wipf P. Trost B.M., Fleming I., Paquette L.A., Comprehensive Organic Synthesis. Vol. 5:1991;827. Chapter 7.2.
    • (1987) Org. React. Mech. , pp. 457
    • Murray, A.W.1
  • 7
    • 0000143928 scopus 로고
    • Reviews: (a) Bartlett P.A. Tetrahedron. 36:1980;3 (b) Gajewski J.J. Hydrocarbon Thermal Isomerizations. 1981;Academic, New York, (c) Lutz R.P. Chem. Rev. 84:1984;205 (d) Hill R.K. Morrison J.D., Asymmetric Synthesis. Vol. 3:1984;503 Academic, New York, (e) Murray A.W. Org. React. Mech. 1986;429 Murray A.W. Org. React. Mech. 1987;457 (f) Moody C.J. Adv. Heterocycl. Chem. 42:1987;203 (g) Ziegler F.E. Chem. Rev. 88:1988;1423 (h) Kallmerten J., Wittman M.D. Stud. Nat. Prod. Chem. 3:1989;233 (i) Blechert S. Synthesis. 1989;71 (j) Wipf P. Trost B.M., Fleming I., Paquette L.A., Comprehensive Organic Synthesis. Vol. 5:1991;827. Chapter 7.2.
    • (1987) Adv. Heterocycl. Chem. , vol.42 , pp. 203
    • Moody, C.J.1
  • 8
    • 33845279007 scopus 로고
    • Reviews: (a) Bartlett P.A. Tetrahedron. 36:1980;3 (b) Gajewski J.J. Hydrocarbon Thermal Isomerizations. 1981;Academic, New York, (c) Lutz R.P. Chem. Rev. 84:1984;205 (d) Hill R.K. Morrison J.D., Asymmetric Synthesis. Vol. 3:1984;503 Academic, New York, (e) Murray A.W. Org. React. Mech. 1986;429 Murray A.W. Org. React. Mech. 1987;457 (f) Moody C.J. Adv. Heterocycl. Chem. 42:1987;203 (g) Ziegler F.E. Chem. Rev. 88:1988;1423 (h) Kallmerten J., Wittman M.D. Stud. Nat. Prod. Chem. 3:1989;233 (i) Blechert S. Synthesis. 1989;71 (j) Wipf P. Trost B.M., Fleming I., Paquette L.A., Comprehensive Organic Synthesis. Vol. 5:1991;827. Chapter 7.2.
    • (1988) Chem. Rev. , vol.88 , pp. 1423
    • Ziegler, F.E.1
  • 9
    • 0000458312 scopus 로고
    • Reviews: (a) Bartlett P.A. Tetrahedron. 36:1980;3 (b) Gajewski J.J. Hydrocarbon Thermal Isomerizations. 1981;Academic, New York, (c) Lutz R.P. Chem. Rev. 84:1984;205 (d) Hill R.K. Morrison J.D., Asymmetric Synthesis. Vol. 3:1984;503 Academic, New York, (e) Murray A.W. Org. React. Mech. 1986;429 Murray A.W. Org. React. Mech. 1987;457 (f) Moody C.J. Adv. Heterocycl. Chem. 42:1987;203 (g) Ziegler F.E. Chem. Rev. 88:1988;1423 (h) Kallmerten J., Wittman M.D. Stud. Nat. Prod. Chem. 3:1989;233 (i) Blechert S. Synthesis. 1989;71 (j) Wipf P. Trost B.M., Fleming I., Paquette L.A., Comprehensive Organic Synthesis. Vol. 5:1991;827. Chapter 7.2.
    • (1989) Stud. Nat. Prod. Chem. , vol.3 , pp. 233
    • Kallmerten, J.1    Wittman, M.D.2
  • 10
    • 85082586002 scopus 로고
    • Reviews: (a) Bartlett P.A. Tetrahedron. 36:1980;3 (b) Gajewski J.J. Hydrocarbon Thermal Isomerizations. 1981;Academic, New York, (c) Lutz R.P. Chem. Rev. 84:1984;205 (d) Hill R.K. Morrison J.D., Asymmetric Synthesis. Vol. 3:1984;503 Academic, New York, (e) Murray A.W. Org. React. Mech. 1986;429 Murray A.W. Org. React. Mech. 1987;457 (f) Moody C.J. Adv. Heterocycl. Chem. 42:1987;203 (g) Ziegler F.E. Chem. Rev. 88:1988;1423 (h) Kallmerten J., Wittman M.D. Stud. Nat. Prod. Chem. 3:1989;233 (i) Blechert S. Synthesis. 1989;71 (j) Wipf P. Trost B.M., Fleming I., Paquette L.A., Comprehensive Organic Synthesis. Vol. 5:1991;827. Chapter 7.2.
    • (1989) Synthesis , pp. 71
    • Blechert, S.1
  • 11
    • 0000217402 scopus 로고
    • B.M. Trost, I. Fleming, & L.A. Paquette Eds. Chapter 7.2
    • Reviews: (a) Bartlett P.A. Tetrahedron. 36:1980;3 (b) Gajewski J.J. Hydrocarbon Thermal Isomerizations. 1981;Academic, New York, (c) Lutz R.P. Chem. Rev. 84:1984;205 (d) Hill R.K. Morrison J.D., Asymmetric Synthesis. Vol. 3:1984;503 Academic, New York, (e) Murray A.W. Org. React. Mech. 1986;429 Murray A.W. Org. React. Mech. 1987;457 (f) Moody C.J. Adv. Heterocycl. Chem. 42:1987;203 (g) Ziegler F.E. Chem. Rev. 88:1988;1423 (h) Kallmerten J., Wittman M.D. Stud. Nat. Prod. Chem. 3:1989;233 (i) Blechert S. Synthesis. 1989;71 (j) Wipf P. Trost B.M., Fleming I., Paquette L.A., Comprehensive Organic Synthesis. Vol. 5:1991;827. Chapter 7.2.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 827
    • Wipf, P.1
  • 15
    • 0011199465 scopus 로고    scopus 로고
    • Ph.D. Dissertation, Nagoya University
    • (d) Saito, S. Ph.D. Dissertation, Nagoya University, 1998.
    • (1998)
    • Saito, S.1
  • 22
    • 0001604466 scopus 로고    scopus 로고
    • and references cited therein
    • Saied, Simard and Wuest elegantly demonstrated that a doubly hydrogen-bonded complex of 3,3,5,5,-tetramethylcyclohexanone can be formed with 2,2′-(1,2-ethynediyl)bis[6-(1,1-dimethylethyl)-4-methylphenol]: Saied O., Simard M., Wuest J.D. J. Org. Chem. 63:1998;3756. and references cited therein.
    • (1998) J. Org. Chem. , vol.63 , pp. 3756
    • Saied, O.1    Simard, M.2    Wuest, J.D.3
  • 25
    • 0011199466 scopus 로고    scopus 로고
    • 3 resulted only in C-O bond cleavage without any rearrangement
    • 3 resulted only in C-O bond cleavage without any rearrangement.


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