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Volumn 52, Issue 27, 1996, Pages 9047-9056

Enhanced diastereoselectivity in the addition of ester enolate to optically active α,β-epoxyaldehydes obtained from nerol and geraniol

Author keywords

diastereoselection; enolate; optically active , epoxy hydroxyesters

Indexed keywords

GERANIOL; NEROL; TERPENE DERIVATIVE;

EID: 0030185484     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00453-X     Document Type: Article
Times cited : (22)

References (27)
  • 2
    • 0000612931 scopus 로고
    • 2 For some publications and references cited therein: Henderson, I.; Sharpless, K.B.; Wong, C.H. J. Am. Chem. Soc. 1994, 116, 558-561. Lin, C.H.; Sugai, T.; Halcomb, R.L.; Ichikawa, Y.; Wong, C.H. J. Am. Chem. Soc. 1992, 114, 10138-10145. Evans, D.A.; Gauchet-Prunet, J.A.; Carreira, E.M.; Charette, A.B. J. Org. Chem. 1991, 56, 741-750. Dondoni, A.J.; Merino, P. Synthesis 1992, 196-200. Roush, W.R.; Straub, J.A.; Vannieuwenhze, M.S. J. Org. Chem. 1991, 56, 1636-1648. Danishefski, S.J. Aldrichim. Acta 1986, 19, 59-69. Braun, M. Angew.Chem.Int.Ed. 1987, 26, 24-37. Nicolaou, K.C. Aldrichim. Acta 1993, 26, 63-77. Danishefsky, S.J.; DeNinno, M.P.; Chen, S.H. J. Am. Chem. Soc. 1988, 110, 3929-3940.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 558-561
    • Henderson, I.1    Sharpless, K.B.2    Wong, C.H.3
  • 3
    • 0000792452 scopus 로고
    • 2 For some publications and references cited therein: Henderson, I.; Sharpless, K.B.; Wong, C.H. J. Am. Chem. Soc. 1994, 116, 558-561. Lin, C.H.; Sugai, T.; Halcomb, R.L.; Ichikawa, Y.; Wong, C.H. J. Am. Chem. Soc. 1992, 114, 10138-10145. Evans, D.A.; Gauchet-Prunet, J.A.; Carreira, E.M.; Charette, A.B. J. Org. Chem. 1991, 56, 741-750. Dondoni, A.J.; Merino, P. Synthesis 1992, 196-200. Roush, W.R.; Straub, J.A.; Vannieuwenhze, M.S. J. Org. Chem. 1991, 56, 1636-1648. Danishefski, S.J. Aldrichim. Acta 1986, 19, 59-69. Braun, M. Angew.Chem.Int.Ed. 1987, 26, 24-37. Nicolaou, K.C. Aldrichim. Acta 1993, 26, 63-77. Danishefsky, S.J.; DeNinno, M.P.; Chen, S.H. J. Am. Chem. Soc. 1988, 110, 3929-3940.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 10138-10145
    • Lin, C.H.1    Sugai, T.2    Halcomb, R.L.3    Ichikawa, Y.4    Wong, C.H.5
  • 4
    • 0026065595 scopus 로고
    • 2 For some publications and references cited therein: Henderson, I.; Sharpless, K.B.; Wong, C.H. J. Am. Chem. Soc. 1994, 116, 558-561. Lin, C.H.; Sugai, T.; Halcomb, R.L.; Ichikawa, Y.; Wong, C.H. J. Am. Chem. Soc. 1992, 114, 10138-10145. Evans, D.A.; Gauchet-Prunet, J.A.; Carreira, E.M.; Charette, A.B. J. Org. Chem. 1991, 56, 741-750. Dondoni, A.J.; Merino, P. Synthesis 1992, 196-200. Roush, W.R.; Straub, J.A.; Vannieuwenhze, M.S. J. Org. Chem. 1991, 56, 1636-1648. Danishefski, S.J. Aldrichim. Acta 1986, 19, 59-69. Braun, M. Angew.Chem.Int.Ed. 1987, 26, 24-37. Nicolaou, K.C. Aldrichim. Acta 1993, 26, 63-77. Danishefsky, S.J.; DeNinno, M.P.; Chen, S.H. J. Am. Chem. Soc. 1988, 110, 3929-3940.
    • (1991) J. Org. Chem. , vol.56 , pp. 741-750
    • Evans, D.A.1    Gauchet-Prunet, J.A.2    Carreira, E.M.3    Charette, A.B.4
  • 5
    • 0026576696 scopus 로고
    • 2 For some publications and references cited therein: Henderson, I.; Sharpless, K.B.; Wong, C.H. J. Am. Chem. Soc. 1994, 116, 558-561. Lin, C.H.; Sugai, T.; Halcomb, R.L.; Ichikawa, Y.; Wong, C.H. J. Am. Chem. Soc. 1992, 114, 10138-10145. Evans, D.A.; Gauchet-Prunet, J.A.; Carreira, E.M.; Charette, A.B. J. Org. Chem. 1991, 56, 741-750. Dondoni, A.J.; Merino, P. Synthesis 1992, 196-200. Roush, W.R.; Straub, J.A.; Vannieuwenhze, M.S. J. Org. Chem. 1991, 56, 1636-1648. Danishefski, S.J. Aldrichim. Acta 1986, 19, 59-69. Braun, M. Angew.Chem.Int.Ed. 1987, 26, 24-37. Nicolaou, K.C. Aldrichim. Acta 1993, 26, 63-77. Danishefsky, S.J.; DeNinno, M.P.; Chen, S.H. J. Am. Chem. Soc. 1988, 110, 3929-3940.
    • (1992) Synthesis , pp. 196-200
    • Dondoni, A.J.1    Merino, P.2
  • 6
    • 33751499016 scopus 로고
    • 2 For some publications and references cited therein: Henderson, I.; Sharpless, K.B.; Wong, C.H. J. Am. Chem. Soc. 1994, 116, 558-561. Lin, C.H.; Sugai, T.; Halcomb, R.L.; Ichikawa, Y.; Wong, C.H. J. Am. Chem. Soc. 1992, 114, 10138-10145. Evans, D.A.; Gauchet-Prunet, J.A.; Carreira, E.M.; Charette, A.B. J. Org. Chem. 1991, 56, 741-750. Dondoni, A.J.; Merino, P. Synthesis 1992, 196-200. Roush, W.R.; Straub, J.A.; Vannieuwenhze, M.S. J. Org. Chem. 1991, 56, 1636-1648. Danishefski, S.J. Aldrichim. Acta 1986, 19, 59-69. Braun, M. Angew.Chem.Int.Ed. 1987, 26, 24-37. Nicolaou, K.C. Aldrichim. Acta 1993, 26, 63-77. Danishefsky, S.J.; DeNinno, M.P.; Chen, S.H. J. Am. Chem. Soc. 1988, 110, 3929-3940.
    • (1991) J. Org. Chem. , vol.56 , pp. 1636-1648
    • Roush, W.R.1    Straub, J.A.2    Vannieuwenhze, M.S.3
  • 7
    • 0023889181 scopus 로고
    • 2 For some publications and references cited therein: Henderson, I.; Sharpless, K.B.; Wong, C.H. J. Am. Chem. Soc. 1994, 116, 558-561. Lin, C.H.; Sugai, T.; Halcomb, R.L.; Ichikawa, Y.; Wong, C.H. J. Am. Chem. Soc. 1992, 114, 10138-10145. Evans, D.A.; Gauchet-Prunet, J.A.; Carreira, E.M.; Charette, A.B. J. Org. Chem. 1991, 56, 741-750. Dondoni, A.J.; Merino, P. Synthesis 1992, 196-200. Roush, W.R.; Straub, J.A.; Vannieuwenhze, M.S. J. Org. Chem. 1991, 56, 1636-1648. Danishefski, S.J. Aldrichim. Acta 1986, 19, 59-69. Braun, M. Angew.Chem.Int.Ed. 1987, 26, 24-37. Nicolaou, K.C. Aldrichim. Acta 1993, 26, 63-77. Danishefsky, S.J.; DeNinno, M.P.; Chen, S.H. J. Am. Chem. Soc. 1988, 110, 3929-3940.
    • (1986) Aldrichim. Acta , vol.19 , pp. 59-69
    • Danishefski, S.J.1
  • 8
    • 84973329202 scopus 로고
    • 2 For some publications and references cited therein: Henderson, I.; Sharpless, K.B.; Wong, C.H. J. Am. Chem. Soc. 1994, 116, 558-561. Lin, C.H.; Sugai, T.; Halcomb, R.L.; Ichikawa, Y.; Wong, C.H. J. Am. Chem. Soc. 1992, 114, 10138-10145. Evans, D.A.; Gauchet-Prunet, J.A.; Carreira, E.M.; Charette, A.B. J. Org. Chem. 1991, 56, 741-750. Dondoni, A.J.; Merino, P. Synthesis 1992, 196-200. Roush, W.R.; Straub, J.A.; Vannieuwenhze, M.S. J. Org. Chem. 1991, 56, 1636-1648. Danishefski, S.J. Aldrichim. Acta 1986, 19, 59-69. Braun, M. Angew.Chem.Int.Ed. 1987, 26, 24-37. Nicolaou, K.C. Aldrichim. Acta 1993, 26, 63-77. Danishefsky, S.J.; DeNinno, M.P.; Chen, S.H. J. Am. Chem. Soc. 1988, 110, 3929-3940.
    • (1987) Angew.chem.int.ed. , vol.26 , pp. 24-37
    • Braun, M.1
  • 9
    • 12044249415 scopus 로고
    • 2 For some publications and references cited therein: Henderson, I.; Sharpless, K.B.; Wong, C.H. J. Am. Chem. Soc. 1994, 116, 558-561. Lin, C.H.; Sugai, T.; Halcomb, R.L.; Ichikawa, Y.; Wong, C.H. J. Am. Chem. Soc. 1992, 114, 10138-10145. Evans, D.A.; Gauchet-Prunet, J.A.; Carreira, E.M.; Charette, A.B. J. Org. Chem. 1991, 56, 741-750. Dondoni, A.J.; Merino, P. Synthesis 1992, 196-200. Roush, W.R.; Straub, J.A.; Vannieuwenhze, M.S. J. Org. Chem. 1991, 56, 1636-1648. Danishefski, S.J. Aldrichim. Acta 1986, 19, 59-69. Braun, M. Angew.Chem.Int.Ed. 1987, 26, 24-37. Nicolaou, K.C. Aldrichim. Acta 1993, 26, 63-77. Danishefsky, S.J.; DeNinno, M.P.; Chen, S.H. J. Am. Chem. Soc. 1988, 110, 3929-3940.
    • (1993) Aldrichim. Acta , vol.26 , pp. 63-77
    • Nicolaou, K.C.1
  • 10
    • 0023889181 scopus 로고
    • 2 For some publications and references cited therein: Henderson, I.; Sharpless, K.B.; Wong, C.H. J. Am. Chem. Soc. 1994, 116, 558-561. Lin, C.H.; Sugai, T.; Halcomb, R.L.; Ichikawa, Y.; Wong, C.H. J. Am. Chem. Soc. 1992, 114, 10138-10145. Evans, D.A.; Gauchet-Prunet, J.A.; Carreira, E.M.; Charette, A.B. J. Org. Chem. 1991, 56, 741-750. Dondoni, A.J.; Merino, P. Synthesis 1992, 196-200. Roush, W.R.; Straub, J.A.; Vannieuwenhze, M.S. J. Org. Chem. 1991, 56, 1636-1648. Danishefski, S.J. Aldrichim. Acta 1986, 19, 59-69. Braun, M. Angew.Chem.Int.Ed. 1987, 26, 24-37. Nicolaou, K.C. Aldrichim. Acta 1993, 26, 63-77. Danishefsky, S.J.; DeNinno, M.P.; Chen, S.H. J. Am. Chem. Soc. 1988, 110, 3929-3940.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 3929-3940
    • Danishefsky, S.J.1    DeNinno, M.P.2    Chen, S.H.3
  • 14
    • 0001618128 scopus 로고
    • b) Paterson, I.; Boddy, I.; Mason, I. Tetrahedron Lett. 1987, 28, 5205-5208, Paterson, I.; Tillyer, R.D.; Smaill J.B. Tetrahedron Lett. 1993, 34, 7137-7140 and references cited therein.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 5205-5208
    • Paterson, I.1    Boddy, I.2    Mason, I.3
  • 15
    • 0027434797 scopus 로고
    • and references cited therein
    • b) Paterson, I.; Boddy, I.; Mason, I. Tetrahedron Lett. 1987, 28, 5205-5208, Paterson, I.; Tillyer, R.D.; Smaill J.B. Tetrahedron Lett. 1993, 34, 7137-7140 and references cited therein.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 7137-7140
    • Paterson, I.1    Tillyer, R.D.2    Smaill, J.B.3
  • 17
    • 0012815040 scopus 로고
    • 6 Gao, Y.; Hanson, R.M.; Klunder, J.M.; Ko, S.Y.; Masamune, H.; Sharpless, K.B. J. Am. Chem. Soc. 1987, 109, 5765-5780. Katsuki, T.; Sharpless, K.B. J. Am. Chem. Soc. 1980, 102, 5974-5976.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 5974-5976
    • Katsuki, T.1    Sharpless, K.B.2
  • 22
    • 49949128203 scopus 로고
    • and 2205-2208
    • 11 Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199-2204 and 2205-2208. Anh, N.T.; Eisenstein, O. Nouv. J. chim. 1977, 1, 61-70. Cornforth, J.W.; Cornforth, R.H.; Methew, K.K. J. Chem. Soc. 1959, 112-116.
    • (1968) Tetrahedron Lett. , pp. 2199-2204
    • Cherest, M.1    Felkin, H.2    Prudent, N.3
  • 23
    • 0002451214 scopus 로고
    • 11 Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199-2204 and 2205-2208. Anh, N.T.; Eisenstein, O. Nouv. J. chim. 1977, 1, 61-70. Cornforth, J.W.; Cornforth, R.H.; Methew, K.K. J. Chem. Soc. 1959, 112-116.
    • (1977) Nouv. J. Chim. , vol.1 , pp. 61-70
    • Anh, N.T.1    Eisenstein, O.2
  • 24
    • 37049057911 scopus 로고
    • 11 Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199-2204 and 2205-2208. Anh, N.T.; Eisenstein, O. Nouv. J. chim. 1977, 1, 61-70. Cornforth, J.W.; Cornforth, R.H.; Methew, K.K. J. Chem. Soc. 1959, 112-116.
    • (1959) J. Chem. Soc. , pp. 112-116
    • Cornforth, J.W.1    Cornforth, R.H.2    Methew, K.K.3
  • 25
    • 0026076172 scopus 로고
    • 9005-9018 and references cited therein
    • 12 Frenking, G.; Köhler, K.F.; Reetz, M.T. Tetrahedron 1991, 47, 8991-9004, 9005-9018 and references cited therein.
    • (1991) Tetrahedron , vol.47 , pp. 8991-9004
    • Frenking, G.1    Köhler, K.F.2    Reetz, M.T.3
  • 26
    • 85030200794 scopus 로고    scopus 로고
    • note
    • 13 Molecular mechanic calculations were obtained from a PC-Model (4.0 version) and a MMX force field Programme of Allinger N.L. modified by Gajiewski J.J. and Gilbert F.E. (Serena Software, Bloomington, USA).
  • 27
    • 85030199627 scopus 로고    scopus 로고
    • note
    • 2Oep:-63° ∼conf. III


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