메뉴 건너뛰기




Volumn 119, Issue 21, 1997, Pages 4900-4910

Reaction pathway of the conjugate addition of lithium organocuprate clusters to acrolein

Author keywords

[No Author keywords available]

Indexed keywords

ACROLEIN; COPPER COMPLEX; LITHIUM DERIVATIVE;

EID: 0030970598     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja964209h     Document Type: Article
Times cited : (113)

References (116)
  • 1
    • 0002563073 scopus 로고
    • Reviews: Posner, G. H. Org. React. 1972, 19, 1-113. Kozlowski, J. A. Comprehensive Organic Synthesis; Trost, B. M., Fleming I., Eds.; Pergamon: Oxford, 1991; Vol. 4, pp 169-198. Organocopper Reagents; Taylor, R. J. K., Ed.; Oxford University Press: UK, 1994.
    • (1972) Org. React. , vol.19 , pp. 1-113
    • Posner, G.H.1
  • 2
    • 0000696943 scopus 로고
    • Trost, B. M., Fleming I., Eds.; Pergamon: Oxford
    • Reviews: Posner, G. H. Org. React. 1972, 19, 1-113. Kozlowski, J. A. Comprehensive Organic Synthesis; Trost, B. M., Fleming I., Eds.; Pergamon: Oxford, 1991; Vol. 4, pp 169-198. Organocopper Reagents; Taylor, R. J. K., Ed.; Oxford University Press: UK, 1994.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 169-198
    • Kozlowski, J.A.1
  • 3
    • 0004228992 scopus 로고
    • Oxford University Press: UK
    • Reviews: Posner, G. H. Org. React. 1972, 19, 1-113. Kozlowski, J. A. Comprehensive Organic Synthesis; Trost, B. M., Fleming I., Eds.; Pergamon: Oxford, 1991; Vol. 4, pp 169-198. Organocopper Reagents; Taylor, R. J. K., Ed.; Oxford University Press: UK, 1994.
    • (1994) Organocopper Reagents
    • Taylor, R.J.K.1
  • 5
    • 33947267238 scopus 로고
    • House, H. O.; Respess, W. L.; Whitesides, G. M. J. Org. Chem. 1966, 31, 3128-3141. Cf.: Gilman, H.; Jones, R. G.; Woods, L. A. J. Org. Chem. 1952, 17, 1630-1634.
    • (1952) J. Org. Chem. , vol.17 , pp. 1630-1634
    • Gilman, H.1    Jones, R.G.2    Woods, L.A.3
  • 6
    • 0001427817 scopus 로고
    • House, H. O.; Umen, M. J. J. Org. Chem. 1973, 38, 3893-3901. House, H. O. Acc. Chem. Res. 1976, 9, 59-67. Smith, R. A. J.; Hannah, D. J. Tetrahedron 1979, 35, 1183-1189.
    • (1973) J. Org. Chem. , vol.38 , pp. 3893-3901
    • House, H.O.1    Umen, M.J.2
  • 7
    • 0002051108 scopus 로고
    • House, H. O.; Umen, M. J. J. Org. Chem. 1973, 38, 3893-3901. House, H. O. Acc. Chem. Res. 1976, 9, 59-67. Smith, R. A. J.; Hannah, D. J. Tetrahedron 1979, 35, 1183-1189.
    • (1976) Acc. Chem. Res. , vol.9 , pp. 59-67
    • House, H.O.1
  • 8
    • 0007003642 scopus 로고
    • House, H. O.; Umen, M. J. J. Org. Chem. 1973, 38, 3893-3901. House, H. O. Acc. Chem. Res. 1976, 9, 59-67. Smith, R. A. J.; Hannah, D. J. Tetrahedron 1979, 35, 1183-1189.
    • (1979) Tetrahedron , vol.35 , pp. 1183-1189
    • Smith, R.A.J.1    Hannah, D.J.2
  • 9
    • 0007003113 scopus 로고
    • Casey, C. P.; Cesa, M. C. J. Am. Chem. Soc. 1979, 101, 4236-4244. Bertz, S. H.; Dabbagh, G.; Cook, J. M.; Honkan, V. J. Org. Chem. 1984, 49, 1739-1743.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 4236-4244
    • Casey, C.P.1    Cesa, M.C.2
  • 17
    • 0001685081 scopus 로고
    • Lorenzen, N. P.; Weiss, E. Angew. Chem., Int. Ed. Engl. 1990, 29, 300-302. Olmstead, M. M.; Power, P. P. Organometallics 1990, 9, 1720-1722.
    • (1990) Organometallics , vol.9 , pp. 1720-1722
    • Olmstead, M.M.1    Power, P.P.2
  • 22
    • 0001038585 scopus 로고
    • Whitesides, G. M.; Fischer, W. F., Jr.; San Filippo, J.; Jr.; Bashe, R. W.; House, H. O. J. Am. Chem. Soc. 1969, 91, 4871-4882. Johnson, C. R.; Dutra, G. A. J. Am. Chem. Soc. 1973, 95, 7777-7782 and 7783-7788. Guo, C.-y.; Brownawell, M. L.; San Filippo, J., Jr.; J. Am. Chem. Soc. 1985, 107, 6028-6030.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 7777-7782
    • Johnson, C.R.1    Dutra, G.A.2
  • 23
    • 0007101617 scopus 로고
    • Whitesides, G. M.; Fischer, W. F., Jr.; San Filippo, J.; Jr.; Bashe, R. W.; House, H. O. J. Am. Chem. Soc. 1969, 91, 4871-4882. Johnson, C. R.; Dutra, G. A. J. Am. Chem. Soc. 1973, 95, 7777-7782 and 7783-7788. Guo, C.-y.; Brownawell, M. L.; San Filippo, J., Jr.; J. Am. Chem. Soc. 1985, 107, 6028-6030.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 6028-6030
    • Guo, C.-Y.1    Brownawell, M.L.2    San Filippo Jr., J.3
  • 28
    • 0346677148 scopus 로고
    • Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1984, 25, 3063-3066. Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6015-6018.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 3063-3066
    • Corey, E.J.1    Boaz, N.W.2
  • 29
    • 6244279150 scopus 로고
    • Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1984, 25, 3063-3066. Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6015-6018.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 6015-6018
    • Corey, E.J.1    Boaz, N.W.2
  • 33
    • 9844239897 scopus 로고
    • McGarrity, J. F.; Ogle, C. A. J. Am. Chem. Soc. 1985, 107, 1805-1810. McGarrity, J. F.; Ogle, C. A.; Brich, Z.; Loosli, H.-R. J. Am. Chem. Soc. 1985, 107, 1810-1815.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 1805-1810
    • McGarrity, J.F.1    Ogle, C.A.2
  • 35
    • 33748240379 scopus 로고
    • Appropriateness of the use of Cu(III) formality has been questioned on the basis of the calculated electron density, which is far less positive (∼+1) than the formal charge of +3. As this proposal neccesarily poses a general question on the use of such a fundamental terminology as "reductive elimination", we employ the conventional notation. See: Snyder, J. P. Angew. Chem., Int. Ed. Engl. 1995, 34, 80-81. Kaupp, M.; von Schnering, H. G. Angew. Chem., Int. Ed. Engl. 1995, 34, 986. Snyder, J. P. Angew. Chem., Int. Ed. Engl. 1995, 34, 986-987.
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 80-81
    • Snyder, J.P.1
  • 36
    • 67049173347 scopus 로고
    • Appropriateness of the use of Cu(III) formality has been questioned on the basis of the calculated electron density, which is far less positive (∼+1) than the formal charge of +3. As this proposal neccesarily poses a general question on the use of such a fundamental terminology as "reductive elimination", we employ the conventional notation. See: Snyder, J. P. Angew. Chem., Int. Ed. Engl. 1995, 34, 80-81. Kaupp, M.; von Schnering, H. G. Angew. Chem., Int. Ed. Engl. 1995, 34, 986. Snyder, J. P. Angew. Chem., Int. Ed. Engl. 1995, 34, 986-987.
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 986
    • Kaupp, M.1    Von Schnering, H.G.2
  • 37
    • 84873995657 scopus 로고
    • Appropriateness of the use of Cu(III) formality has been questioned on the basis of the calculated electron density, which is far less positive (∼+1) than the formal charge of +3. As this proposal neccesarily poses a general question on the use of such a fundamental terminology as "reductive elimination", we employ the conventional notation. See: Snyder, J. P. Angew. Chem., Int. Ed. Engl. 1995, 34, 80-81. Kaupp, M.; von Schnering, H. G. Angew. Chem., Int. Ed. Engl. 1995, 34, 986. Snyder, J. P. Angew. Chem., Int. Ed. Engl. 1995, 34, 986-987.
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 986-987
    • Snyder, J.P.1
  • 38
    • 37049086566 scopus 로고
    • Three examples of crystal structures of Cu(III) organocopper species have reported: Willert-Porada, M. A.; Burton, D. J.; Baenziger, N. C. J. Chem. Soc., Chem. Commun. 1989, 1633-1634. Neumann, D.; Roy, T.; Tebbe, K.-F.; Crump, W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1482-1483. Eujen, R.; Hoge, B.; Brauer, D. J. J. Organomet. Chem. 1996, 519, 7-20.
    • (1989) J. Chem. Soc., Chem. Commun. , pp. 1633-1634
    • Willert-Porada, M.A.1    Burton, D.J.2    Baenziger, N.C.3
  • 39
    • 33748248378 scopus 로고
    • Three examples of crystal structures of Cu(III) organocopper species have reported: Willert-Porada, M. A.; Burton, D. J.; Baenziger, N. C. J. Chem. Soc., Chem. Commun. 1989, 1633-1634. Neumann, D.; Roy, T.; Tebbe, K.-F.; Crump, W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1482-1483. Eujen, R.; Hoge, B.; Brauer, D. J. J. Organomet. Chem. 1996, 519, 7-20.
    • (1993) Angew. Chem., Int. Ed. Engl. , vol.32 , pp. 1482-1483
    • Neumann, D.1    Roy, T.2    Tebbe, K.-F.3    Crump, W.4
  • 40
    • 0030602663 scopus 로고    scopus 로고
    • Three examples of crystal structures of Cu(III) organocopper species have reported: Willert-Porada, M. A.; Burton, D. J.; Baenziger, N. C. J. Chem. Soc., Chem. Commun. 1989, 1633-1634. Neumann, D.; Roy, T.; Tebbe, K.-F.; Crump, W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1482-1483. Eujen, R.; Hoge, B.; Brauer, D. J. J. Organomet. Chem. 1996, 519, 7-20.
    • (1996) J. Organomet. Chem. , vol.519 , pp. 7-20
    • Eujen, R.1    Hoge, B.2    Brauer, D.J.3
  • 41
    • 1842301134 scopus 로고    scopus 로고
    • For alkyl cuprates other than methylcuprate, or if the copper reagent is adequately solubilized with a ligand, the alkyl copper remains in solution
    • For alkyl cuprates other than methylcuprate, or if the copper reagent is adequately solubilized with a ligand, the alkyl copper remains in solution.
  • 45
    • 0000916779 scopus 로고
    • 3SiCl (Chuit, C.; Foulon, J. P.; Normant, J. F. Tetrahedron 1980, 36, 2305-2310. See also: Nakamura, E. In Organocopper Reagents; Taylor, R. J. K., Ed.; Oxford University Press: UK, 1994; Chapter 6, pp 129-142.).
    • (1980) Tetrahedron , vol.36 , pp. 2305-2310
    • Chuit, C.1    Foulon, J.P.2    Normant, J.F.3
  • 46
    • 0000916779 scopus 로고
    • Taylor, R. J. K., Ed.; Oxford University Press: UK, Chapter 6
    • 3SiCl (Chuit, C.; Foulon, J. P.; Normant, J. F. Tetrahedron 1980, 36, 2305-2310. See also: Nakamura, E. In Organocopper Reagents; Taylor, R. J. K., Ed.; Oxford University Press: UK, 1994; Chapter 6, pp 129-142.).
    • (1994) Organocopper Reagents , pp. 129-142
    • Nakamura, E.1
  • 47
    • 0001606689 scopus 로고
    • Lipshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. A. Tetrahedron 1984, 40, 5005-5038. Lipshutz, B. H.; Sharma, S.; Ellsworth, E. L. J. Am. Chem. Soc. 1990, 112, 4032-4034. Lipshutz, B. H.; James, B. J. Org. Chem. 1994, 59, 7585-7587. Lipshutz, B. H.; Stevens, K. L.; James, B.; Pavlovich, J. G.; Snyder, J. P. J. Am. Chem. Soc. 1996, 118, 6796-6797.
    • (1984) Tetrahedron , vol.40 , pp. 5005-5038
    • Lipshutz, B.H.1    Wilhelm, R.S.2    Kozlowski, J.A.3
  • 48
    • 0000500504 scopus 로고
    • Lipshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. A. Tetrahedron 1984, 40, 5005-5038. Lipshutz, B. H.; Sharma, S.; Ellsworth, E. L. J. Am. Chem. Soc. 1990, 112, 4032-4034. Lipshutz, B. H.; James, B. J. Org. Chem. 1994, 59, 7585-7587. Lipshutz, B. H.; Stevens, K. L.; James, B.; Pavlovich, J. G.; Snyder, J. P. J. Am. Chem. Soc. 1996, 118, 6796-6797.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 4032-4034
    • Lipshutz, B.H.1    Sharma, S.2    Ellsworth, E.L.3
  • 49
    • 0000503684 scopus 로고
    • Lipshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. A. Tetrahedron 1984, 40, 5005-5038. Lipshutz, B. H.; Sharma, S.; Ellsworth, E. L. J. Am. Chem. Soc. 1990, 112, 4032-4034. Lipshutz, B. H.; James, B. J. Org. Chem. 1994, 59, 7585-7587. Lipshutz, B. H.; Stevens, K. L.; James, B.; Pavlovich, J. G.; Snyder, J. P. J. Am. Chem. Soc. 1996, 118, 6796-6797.
    • (1994) J. Org. Chem. , vol.59 , pp. 7585-7587
    • Lipshutz, B.H.1    James, B.2
  • 50
    • 0029949483 scopus 로고    scopus 로고
    • Lipshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. A. Tetrahedron 1984, 40, 5005-5038. Lipshutz, B. H.; Sharma, S.; Ellsworth, E. L. J. Am. Chem. Soc. 1990, 112, 4032-4034. Lipshutz, B. H.; James, B. J. Org. Chem. 1994, 59, 7585-7587. Lipshutz, B. H.; Stevens, K. L.; James, B.; Pavlovich, J. G.; Snyder, J. P. J. Am. Chem. Soc. 1996, 118, 6796-6797.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 6796-6797
    • Lipshutz, B.H.1    Stevens, K.L.2    James, B.3    Pavlovich, J.G.4    Snyder, J.P.5
  • 59
    • 0030443479 scopus 로고    scopus 로고
    • correction
    • (h) Huang, H.; Alvarez, K.; Cui, Q.; Barnhart, T. M.; Snyder, J. P.; Penner-Hahn J. E. J. Am. Chem. Soc. 1996, 118, 8808-8816, and 1996, 118, 12252 (correction).
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 12252
  • 61
    • 6944251055 scopus 로고
    • MP2(FC) (FC = frozen core): Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618-622. Pople, J. A.; Krishman, R.; Schlegel, H. B.; Brinkley, J. S. Int. J. Quantum. Chem. Symp. 1979, 13, 225-241.
    • (1934) Phys. Rev. , vol.46 , pp. 618-622
    • Møller, C.1    Plesset, M.S.2
  • 63
    • 0000189651 scopus 로고
    • (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B, 1988, 37, 785-789.
    • (1993) J. Chem. Phys. , vol.98 , pp. 5648-5652
    • Becke, A.D.1
  • 64
    • 0345491105 scopus 로고
    • (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B, 1988, 37, 785-789.
    • (1988) Phys. Rev. B , vol.37 , pp. 785-789
    • Lee, C.1    Yang, W.2    Parr, R.G.3
  • 68
    • 0011083499 scopus 로고    scopus 로고
    • Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926. NBO Version 3.1 in Gaussian 94 package; implemented by Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F.
    • (1988) Chem. Rev. , vol.88 , pp. 899-926
    • Reed, A.E.1    Curtiss, L.A.2    Weinhold, F.3
  • 70
    • 33751044609 scopus 로고
    • Fukui, K. Acc. Chem. Res. 1981, 14, 363-368. Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154-2161. Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527.
    • (1981) Acc. Chem. Res. , vol.14 , pp. 363-368
    • Fukui, K.1
  • 71
    • 36549095692 scopus 로고
    • Fukui, K. Acc. Chem. Res. 1981, 14, 363-368. Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154-2161. Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527.
    • (1989) J. Chem. Phys. , vol.90 , pp. 2154-2161
    • Gonzalez, C.1    Schlegel, H.B.2
  • 72
    • 33750614386 scopus 로고
    • Fukui, K. Acc. Chem. Res. 1981, 14, 363-368. Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154-2161. Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527.
    • (1990) J. Phys. Chem. , vol.94 , pp. 5523-5527
    • Gonzalez, C.1    Schlegel, H.B.2
  • 75
    • 0042113153 scopus 로고
    • Kohn, W.; Sham, L. J. Phys. Rev. 1965, 140, A1133-A1138. Boys, S. F. Quantum Theory of Atoms, Molecules, and the Solid State; Lowdin. P.O.; Ed.; Academic Press: New York, USA, 1968, pp 253-262. Haddon, R. C.; Williams, G. R. J. Chem. Phys. Lett. 1976, 42, 453-455.
    • (1965) Phys. Rev. , vol.140
    • Kohn, W.1    Sham, L.J.2
  • 76
    • 0002367580 scopus 로고
    • Lowdin. P.O.; Ed.; Academic Press: New York, USA
    • Kohn, W.; Sham, L. J. Phys. Rev. 1965, 140, A1133-A1138. Boys, S. F. Quantum Theory of Atoms, Molecules, and the Solid State; Lowdin. P.O.; Ed.; Academic Press: New York, USA, 1968, pp 253-262. Haddon, R. C.; Williams, G. R. J. Chem. Phys. Lett. 1976, 42, 453-455.
    • (1968) Quantum Theory of Atoms, Molecules, and the Solid State , pp. 253-262
    • Boys, S.F.1
  • 77
    • 0001518218 scopus 로고
    • Kohn, W.; Sham, L. J. Phys. Rev. 1965, 140, A1133-A1138. Boys, S. F. Quantum Theory of Atoms, Molecules, and the Solid State; Lowdin. P.O.; Ed.; Academic Press: New York, USA, 1968, pp 253-262. Haddon, R. C.; Williams, G. R. J. Chem. Phys. Lett. 1976, 42, 453-455.
    • (1976) Chem. Phys. Lett. , vol.42 , pp. 453-455
    • Haddon, R.C.1    Williams, G.R.J.2
  • 79
    • 1242268874 scopus 로고    scopus 로고
    • We thank Dr. M. J. Frisch for a preprint before publication
    • Cheeseman, J. R.; Trucks, G. W.; Keith, T. A.; Frisch, M. J. J. Chem. Phys. 1996, 104, 5497-5509. We thank Dr. M. J. Frisch for a preprint before publication.
    • (1996) J. Chem. Phys. , vol.104 , pp. 5497-5509
    • Cheeseman, J.R.1    Trucks, G.W.2    Keith, T.A.3    Frisch, M.J.4
  • 82
    • 0001273451 scopus 로고
    • (c) Nakamura, M.; Nakamura, E.; Koga, N., Morokuma, K. J. Am. Chem. Soc. 1993, 115, 11016-11017. Nakamura, M.; Nakamura, E.; Koga, N.; Morokuma, K. J. Chem. Soc., Faraday Trans., 1994, 90, 1789-1798.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 11016-11017
    • Nakamura, M.1    Nakamura, E.2    Koga, N.3    Morokuma, K.4
  • 86
    • 0001741843 scopus 로고
    • House, H. O.; Wilkins, J. M.; J. Org. Chem. 1978, 43, 2443-2454. Cf.: Klein, J.; Levene, R. J. Chem. Soc., Perkin II 1973, 1971-1978.
    • (1978) J. Org. Chem. , vol.43 , pp. 2443-2454
    • House, H.O.1    Wilkins, J.M.2
  • 90
    • 1842294605 scopus 로고    scopus 로고
    • The solvated dimer shown in Figure 4 is an isomer of the previously reported solvated one (refs 10 and 11). The present isomer is 0.7 kcal/mol more stable than the previous at the B3LYP/321A//B3LYP/321A level
    • The solvated dimer shown in Figure 4 is an isomer of the previously reported solvated one (refs 10 and 11). The present isomer is 0.7 kcal/mol more stable than the previous at the B3LYP/321A//B3LYP/321A level.
  • 91
    • 1842413118 scopus 로고    scopus 로고
    • Most of the stationary points in this and the preceding article (ref 9) were investigated both at the B3LYP/631A and B3LYP/321A levels (only some representative data shown in Table 1 in the preceding article). The geometries were very similar to each other, allowing qualitative comparison of structural data at different levels. The qualitative energy profiles were also the same for both levels of theory, though there were considerable difference in the absolute magnitude of energies (relative to reactants). This difference is likely due to the deficiency of the 321A basis set in evaluating lithium-oxygen and copper-olefin interactions
    • Most of the stationary points in this and the preceding article (ref 9) were investigated both at the B3LYP/631A and B3LYP/321A levels (only some representative data shown in Table 1 in the preceding article). The geometries were very similar to each other, allowing qualitative comparison of structural data at different levels. The qualitative energy profiles were also the same for both levels of theory, though there were considerable difference in the absolute magnitude of energies (relative to reactants). This difference is likely due to the deficiency of the 321A basis set in evaluating lithium-oxygen and copper-olefin interactions.
  • 93
    • 1842289238 scopus 로고    scopus 로고
    • Experiments did not tell if this is a cuprate/enone complex or simply a lithium halide/enone complex
    • Experiments did not tell if this is a cuprate/enone complex or simply a lithium halide/enone complex.
  • 96
    • 1842291591 scopus 로고    scopus 로고
    • We found little biradical character in the complexes and the TSs as shown by the lack of RB3LYP-UB3LYP instability (vide supra)
    • We found little biradical character in the complexes and the TSs as shown by the lack of RB3LYP-UB3LYP instability (vide supra).
  • 99
    • 0001628097 scopus 로고
    • Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1995, 117, 2166-2178. Henderson, K. W.; Dorigo, A. E.; Liu, Q.-Y.; Willard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339-1347.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 2166-2178
    • Romesberg, F.E.1    Collum, D.B.2
  • 103
    • 0001040147 scopus 로고
    • Cf.: Reviews: Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771-806. Kanai, T.; Nakagawa, Y.; Tomioka, K. J. Syn. Org. Chem. Jpn. 1996, 35, 474-480. van Koten, G. Pure Appl. Chem. 1994, 66, 1455-1462.
    • (1992) Chem. Rev. , vol.92 , pp. 771-806
    • Rossiter, B.E.1    Swingle, N.M.2
  • 104
    • 0030167855 scopus 로고    scopus 로고
    • Cf.: Reviews: Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771-806. Kanai, T.; Nakagawa, Y.; Tomioka, K. J. Syn. Org. Chem. Jpn. 1996, 35, 474-480. van Koten, G. Pure Appl. Chem. 1994, 66, 1455-1462.
    • (1996) J. Syn. Org. Chem. Jpn. , vol.35 , pp. 474-480
    • Kanai, T.1    Nakagawa, Y.2    Tomioka, K.3
  • 105
    • 2342469105 scopus 로고
    • Cf.: Reviews: Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771-806. Kanai, T.; Nakagawa, Y.; Tomioka, K. J. Syn. Org. Chem. Jpn. 1996, 35, 474-480. van Koten, G. Pure Appl. Chem. 1994, 66, 1455-1462.
    • (1994) Pure Appl. Chem. , vol.66 , pp. 1455-1462
    • Van Koten, G.1
  • 106
    • 0000224619 scopus 로고
    • (a) Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1984, 106, 3368-3370. Horiguchi, Y.; Matsuzawa, S.; Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1986, 27, 4025-4028. Nakamura, E.; Matsuzawa, S.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1986, 27, 4029-4032.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 3368-3370
    • Nakamura, E.1    Kuwajima, I.2
  • 107
    • 0001249846 scopus 로고
    • (a) Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1984, 106, 3368-3370. Horiguchi, Y.; Matsuzawa, S.; Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1986, 27, 4025-4028. Nakamura, E.; Matsuzawa, S.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1986, 27, 4029-4032.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 4025-4028
    • Horiguchi, Y.1    Matsuzawa, S.2    Nakamura, E.3    Kuwajima, I.4
  • 108
    • 0001080242 scopus 로고
    • (a) Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1984, 106, 3368-3370. Horiguchi, Y.; Matsuzawa, S.; Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1986, 27, 4025-4028. Nakamura, E.; Matsuzawa, S.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1986, 27, 4029-4032.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 4029-4032
    • Nakamura, E.1    Matsuzawa, S.2    Horiguchi, Y.3    Kuwajima, I.4
  • 109
    • 6244279150 scopus 로고
    • (b) See, also: Corey, E. J.; Boaz, N. W. Tetrahedron Lett, 1985, 26, 6015-6018 and 6019-6022. Alexakis, A.; Berlan, J.; Besace, Y. Tetrahedron Lett. 1986, 27, 1047-1050. Johnson, C. R.; Marren, T. J. Tetrahedron Lett. 1987, 28, 27-30. Horiguchi, Y.; Komatsu, M.; Kuwajima, I. Tetrahedron Lett. 1989, 30, 7087-7090.
    • (1985) Tetrahedron Lett , vol.26 , pp. 6015-6018
    • Corey, E.J.1    Boaz, N.W.2
  • 110
    • 0000024394 scopus 로고
    • (b) See, also: Corey, E. J.; Boaz, N. W. Tetrahedron Lett, 1985, 26, 6015-6018 and 6019-6022. Alexakis, A.; Berlan, J.; Besace, Y. Tetrahedron Lett. 1986, 27, 1047-1050. Johnson, C. R.; Marren, T. J. Tetrahedron Lett. 1987, 28, 27-30. Horiguchi, Y.; Komatsu, M.; Kuwajima, I. Tetrahedron Lett. 1989, 30, 7087-7090.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 1047-1050
    • Alexakis, A.1    Berlan, J.2    Besace, Y.3
  • 111
    • 0001862706 scopus 로고
    • (b) See, also: Corey, E. J.; Boaz, N. W. Tetrahedron Lett, 1985, 26, 6015-6018 and 6019-6022. Alexakis, A.; Berlan, J.; Besace, Y. Tetrahedron Lett. 1986, 27, 1047-1050. Johnson, C. R.; Marren, T. J. Tetrahedron Lett. 1987, 28, 27-30. Horiguchi, Y.; Komatsu, M.; Kuwajima, I. Tetrahedron Lett. 1989, 30, 7087-7090.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 27-30
    • Johnson, C.R.1    Marren, T.J.2
  • 112
    • 0024826452 scopus 로고
    • (b) See, also: Corey, E. J.; Boaz, N. W. Tetrahedron Lett, 1985, 26, 6015-6018 and 6019-6022. Alexakis, A.; Berlan, J.; Besace, Y. Tetrahedron Lett. 1986, 27, 1047-1050. Johnson, C. R.; Marren, T. J. Tetrahedron Lett. 1987, 28, 27-30. Horiguchi, Y.; Komatsu, M.; Kuwajima, I. Tetrahedron Lett. 1989, 30, 7087-7090.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 7087-7090
    • Horiguchi, Y.1    Komatsu, M.2    Kuwajima, I.3
  • 113
  • 115
    • 0040427119 scopus 로고
    • (d) For some mechanistic proposals, see: Lipshutz, B. H.; Dimock, S. H.; James, B. J. Am. Chem. Soc. 1993, 115, 9283-9284. Bertz, S. H.; Miao, G.; Rossiter, B. E.; Snyder, J. P. J. Am. Chem. Soc. 1995, 117, 11023-11024.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 9283-9284
    • Lipshutz, B.H.1    Dimock, S.H.2    James, B.3
  • 116
    • 0000813254 scopus 로고
    • (d) For some mechanistic proposals, see: Lipshutz, B. H.; Dimock, S. H.; James, B. J. Am. Chem. Soc. 1993, 115, 9283-9284. Bertz, S. H.; Miao, G.; Rossiter, B. E.; Snyder, J. P. J. Am. Chem. Soc. 1995, 117, 11023-11024.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 11023-11024
    • Bertz, S.H.1    Miao, G.2    Rossiter, B.E.3    Snyder, J.P.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.