메뉴 건너뛰기




Volumn 19, Issue , 2007, Pages 227-407

Stereochemistry of the Base-Promoted Michael Addition Reaction

Author keywords

Diactivated acceptors; Dithioester enethiolates; Driving force; Ester amide enolates; Retro michael addition

Indexed keywords

AMIDES;

EID: 85050326125     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470147283.ch5     Document Type: Chapter
Times cited : (184)

References (412)
  • 9
    • 84980124089 scopus 로고
    • Michael, A. Chem. Ber. 1894, 27, 2126-2130.
    • (1894) Chem. Ber , vol.27 , pp. 2126-2130
    • Michael, A.1
  • 10
    • 84981753307 scopus 로고
    • Michael, A. Chem. Ber. 1900, 33, 3731-3769.
    • (1900) Chem. Ber , vol.33 , pp. 3731-3769
    • Michael, A.1
  • 13
    • 85080397972 scopus 로고
    • For example see, Morrison, J. D., Ed.; Academic: New York, Chapter 1
    • For example see: Evans, D. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1983; Vol. 3, Chapter 1.
    • (1983) Asymmetric Synthesis; , vol.3
    • Evans, D.A.1
  • 15
    • 85050329923 scopus 로고
    • For a review see, Chapter 1
    • For a review see: Posner, G. H. Org. React. 1972, 19, Chapter 1.
    • (1972) Org. React , pp. 19
    • Posner, G.H.1
  • 20
    • 85080431066 scopus 로고
    • Morrison, J. D., Ed.; Academic: New York, Chapter 8
    • Posner, G. H. InAsymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1983; Vol. 2, Chapter 8.
    • (1983) InAsymmetric Synthesis; , vol.2
    • Posner, G.H.1
  • 21
    • 85080391449 scopus 로고
    • Morrison, I. D., Ed.; Academic: New York, Chapter 7
    • Tomioka, K.; Koga, K. In Asymmetric Synthesis; Morrison, I. D., Ed.; Academic: New York, 1983; Vol. 7, Chapter 7.
    • (1983) Asymmetric Synthesis; , vol.7
    • Tomioka, K.1    Koga, K.2
  • 24
    • 85011238600 scopus 로고
    • We are indebted to Mr. Ichiro Mori for translating this Japanese-language review
    • Yamaguchi, M. Yuki Gosei Kagaku 1986, 44, 405-420. We are indebted to Mr. Ichiro Mori for translating this Japanese-language review.
    • (1986) Yuki Gosei Kagaku , vol.44 , pp. 405-420
    • Yamaguchi, M.1
  • 52
    • 33947292848 scopus 로고
    • Eliel, E.J. Chem. Ed. 1971, 48, 163-167.
    • (1971) Chem. Ed , vol.48 , pp. 163-167
    • Eliel, E.J.1
  • 55
    • 0009529363 scopus 로고
    • Angew. Chem. 1980, 92, 573-575.
    • (1980) Angew. Chem , vol.92 , pp. 573-575
  • 56
    • 85080359215 scopus 로고
    • Morrison, J. D., Ed.; Academic: New York, Chapter 2
    • Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1983; Vol. 3, Chapter 2.
    • (1983) Asymmetric Synthesis; , vol.3
    • Heathcock, C.H.1
  • 58
    • 0009924476 scopus 로고
    • In this chapter, we utilize terminology suggested by Mislow and Siegel
    • In this chapter, we utilize terminology suggested by Mislow and Siegel: Mislow, K.; Siegel, J. J. Am. Chem. Soc. 1984, 706, 3319-3328.
    • (1984) J. Am. Chem. Soc , vol.706 , pp. 3319-3328
    • Mislow, K.1    Siegel, J.2
  • 62
    • 33748560899 scopus 로고
    • Angew. Chem. 1985, 97, 1-31.
    • (1985) Angew. Chem , vol.97 , pp. 1-31
  • 66
    • 10844270846 scopus 로고
    • For leading references for the closely related studies of the asymmetric Michael addition of nitromethane to chalcone see
    • For leading references for the closely related studies of the asymmetric Michael addition of nitromethane to chalcone see: Colonna, S.; Hiemstra, H.; Wynberg, H. J. Chem. Soc. Chem. Commun. 1978, 238-239.
    • (1978) J. Chem. Soc. Chem. Commun , pp. 238-239
    • Colonna, S.1    Hiemstra, H.2    Wynberg, H.3
  • 71
    • 85080334423 scopus 로고
    • Eliel, E. L.; Wilen, S. H.; Allinger, N. L.; Eds.; Wiley: New York, Chapter 2
    • Wynberg, H. Topics in Stereochemistry; Eliel, E. L.; Wilen, S. H.; Allinger, N. L.; Eds.; Wiley: New York, 1986; Vol. 16, Chapter 2.
    • (1986) Topics in Stereochemistry; , vol.16
    • Wynberg, H.1
  • 72
    • 37049096703 scopus 로고
    • While reasonable enatiomeric excesses were found with methyl vinyl ketones, very low selectivity was found for the addition of similar substrates to α,β-unsaturated sulfoximides
    • While reasonable enatiomeric excesses were found with methyl vinyl ketones, very low selectivity was found for the addition of similar substrates to α,β-unsaturated sulfoximides: Annunziata, R.; Cinquini, M.; Colonna, S.J. Chem. Soc. Perkin Trans 1 1980, 2422-2424.
    • (1980) Chem. Soc. Perkin Trans 1 , pp. 2422-2424
    • Annunziata, R.1    Cinquini, M.2    Colonna, S.J.3
  • 78
    • 0009665462 scopus 로고
    • For a related study see:
    • For a related study see: Kobayashi, N.; Iwai, K. Tetrahedron Lett. 1980, 21, 2167-2170.
    • (1980) Tetrahedron Lett , vol.21 , pp. 2167-2170
    • Kobayashi, N.1    Iwai, K.2
  • 81
    • 0000377297 scopus 로고
    • Angew. Chem. 1984, 96, 305-306.
    • (1984) Angew. Chem , vol.96 , pp. 305-306
  • 84
    • 0001028942 scopus 로고
    • Angew. Chem. 1986, 98, 442-443.
    • (1986) Angew. Chem , vol.98 , pp. 442-443
  • 92
    • 0001278197 scopus 로고
    • For a related study where preferential addition occurs from one face on a cycloheptanone with a pre-existing stereocenter see
    • For a related study where preferential addition occurs from one face on a cycloheptanone with a pre-existing stereocenter see: Marshall, J. A.; Partridge, J. J. Tetrahedron 1969, 25, 2159-2192.
    • (1969) Tetrahedron , vol.25 , pp. 2159-2192
    • Marshall, J.A.1    Partridge, J.J.2
  • 94
    • 33845280221 scopus 로고
    • For analogous alkylations of this lactone see:
    • For analogous alkylations of this lactone see: Tomioka, K.; Cho, Y.-S.; Sato, F.; Koga, K. J. Org. Chem. 1988, 53, 4094-4098.
    • (1988) J. Org. Chem , vol.53 , pp. 4094-4098
    • Tomioka, K.1    Cho, Y.-S.2    Sato, F.3    Koga, K.4
  • 104
    • 85077702395 scopus 로고
    • For a review of enantioselective synthesis using optically active sulfoxides see
    • For a review of enantioselective synthesis using optically active sulfoxides see: Solladié, G. Synthesis 1981, 185-196.
    • (1981) Synthesis , pp. 185-196
    • Solladié, G.1
  • 105
    • 0000101704 scopus 로고
    • Morrison, J. D., Ed.; Academic: Orlando, Florida, Chapter 2
    • Barbachyn, M. R.; Johnson, C. R. InAsymmetric Synthesis; Morrison, J. D., Ed.; Academic: Orlando, Florida; 1984, Vol. 4, Chapter 2.
    • (1984) InAsymmetric Synthesis; , vol.4
    • Barbachyn, M.R.1    Johnson, C.R.2
  • 106
    • 85080383179 scopus 로고
    • Morrison, J. D., Ed.; Academic: Orlando, Florida;, Chapter 6
    • Solladié, G. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: Orlando, Florida; 1983, Vol. 2, Chapter 6.
    • (1983) Asymmetric Synthesis; , vol.2
    • Solladié, G.1
  • 107
    • 0000474038 scopus 로고
    • Allinger, N. L.; Eliel, E. L.; Wilen, S. H., Eds.; Wiley: New York, New York
    • Mikołajczyk, M.; Dravowicz, J. In Topics in Stereo-chemistry; Allinger, N. L.; Eliel, E. L.; Wilen, S. H., Eds.; Wiley: New York, New York; 1982, Vol. 13, 333-468.
    • (1982) Topics in Stereo-chemistry; , vol.13 , pp. 333-468
    • Mikołajczyk, M.1    Dravowicz, J.2
  • 114
    • 0007237848 scopus 로고
    • For a related study of the Michael addition of thiophenol see
    • For a related study of the Michael addition of thiophenol see: Abramovitch, R. A.; Singer, S. S. J. Org. Chem. 1976,47, 1712-1717.
    • (1976) J. Org. Chem , vol.47 , pp. 1712-1717
    • Abramovitch, R.A.1    Singer, S.2
  • 124
    • 33947469281 scopus 로고
    • and references therein
    • Corey, E. J. J. Am. Chem. Soc. 1955, 77, 1044-1045 and references therein
    • (1955) J. Am. Chem. Soc , vol.77 , pp. 1044-1045
    • Corey, E.J.1
  • 125
    • 33947456315 scopus 로고
    • and references therein
    • Ralls, J. W. J. Am. Chem. Soc. 1953, 75, 2123-2125 and references therein.
    • (1953) J. Am. Chem. Soc , vol.75 , pp. 2123-2125
    • Ralls, J.W.1
  • 126
    • 0345339911 scopus 로고
    • For addition to α,β-unsaturated ketones see
    • For addition to α,β-unsaturated ketones see: Mukaiyama, T.; Hirako, Y.; Takeda, T. Chem. Lett. 1978, 461-464.
    • (1978) Chem. Lett , pp. 461-464
    • Mukaiyama, T.1    Hirako, Y.2    Takeda, T.3
  • 127
    • 84916515730 scopus 로고
    • For a correction of the enantioselectivities reported in part a and the addition to 1-nitrocyclohexene see
    • For a correction of the enantioselectivities reported in part a and the addition to 1-nitrocyclohexene see: Takeda, T.; Hoshiko, T.; Mukaiyama, T. Chem. Lett. 1981, 797-800.
    • (1981) Chem. Lett , pp. 797-800
    • Takeda, T.1    Hoshiko, T.2    Mukaiyama, T.3
  • 129
    • 84985072002 scopus 로고
    • For the related addition of a formyl anion equivalent see
    • For the related addition of a formyl anion equivalent see: Colombo, L.; Gennari, C; Resnati, G.; Seolastico, C. Synthesis 1981, 74-76.
    • (1981) Synthesis , pp. 74-76
    • Colombo, L.1    Gennari, C.2    Resnati, G.3    Seolastico, C.4
  • 134
    • 0000296850 scopus 로고
    • For regiochemical considerations see
    • For regiochemical considerations see: d'Angelo, J. Tetrahedron 1976, 32, 2979-2990.
    • (1976) Tetrahedron , vol.32 , pp. 2979-2990
    • D'Angelo, J.1
  • 152
    • 0002292348 scopus 로고
    • For reviews of the Robinson annelation see
    • For reviews of the Robinson annelation see: Jung, M. E. Tetrahedron 1976, 32, 3-31.
    • (1976) Tetrahedron , vol.32 , pp. 3-31
    • Jung, M.E.1
  • 154
    • 0001033553 scopus 로고
    • For a review of the synthesis of polycarbocyclic sesquiterpenes in which stereoselective an-nelations are discussed see
    • For a review of the synthesis of polycarbocyclic sesquiterpenes in which stereoselective an-nelations are discussed see: Vandewalle, M.; De Clercq, P. Tetrahedron 1985, 41, 1767-1831.
    • (1985) Tetrahedron , vol.41 , pp. 1767-1831
    • Vandewalle, M.1    De Clercq, P.2
  • 155
    • 0013940414 scopus 로고
    • For some examples of stereochemical control with respect to a pre-existing stereocenter in a ring see:
    • For some examples of stereochemical control with respect to a pre-existing stereocenter in a ring see: Ireland, R. E.; Kierstead, R. C. J. Org. Chem. 1966, 31, 2543-2559.
    • (1966) J. Org. Chem , vol.31 , pp. 2543-2559
    • Ireland, R.E.1    Kierstead, R.C.2
  • 162
    • 33847578369 scopus 로고
    • Angew. Chem. 1965, 77, 185-205.
    • (1965) Angew. Chem , vol.77 , pp. 185-205
  • 168
    • 37049131353 scopus 로고
    • For a related approach to products with a similar structure that does not use a stereoselective Michael addition see
    • For a related approach to products with a similar structure that does not use a stereoselective Michael addition see: Hale, R. L.; Zalkow, L. H. J. Chem. Soc, Chem. Commun. 1968, 1249-1250.
    • (1968) J. Chem. Soc, Chem. Commun , pp. 1249-1250
    • Hale, R.L.1    Zalkow, L.H.2
  • 173
    • 0018580471 scopus 로고
    • In these examples, good stereoselectivity with respect to a pre-existing stereocenter in the cyclohexanone is observed
    • Boeckman, R. K., Jr.; Blum, D. M.; Arthur, S. D.J. Am. Chem. Soc. 1979,101, 5060-5062. In these examples, good stereoselectivity with respect to a pre-existing stereocenter in the cyclohexanone is observed.
    • (1979) Am. Chem. Soc , vol.101 , pp. 5060-5062
    • Boeckman, R.K.1    Blum, D.M.2    Arthur, S.D.J.3
  • 174
    • 0000069228 scopus 로고
    • For a recent enantioselective application of this technology see:
    • For a recent enantioselective application of this technology see: Takahashi, T.; Oku-moto, H.; Tsuji, J.; Harada, N. J. Org. Chem. 1984, 49, 948-950.
    • (1984) J. Org. Chem , vol.49 , pp. 948-950
    • Takahashi, T.1    Oku-moto, H.2    Tsuji, J.3    Harada, N.4
  • 177
    • 49949120530 scopus 로고
    • For a related approach where facial selectivity with respect to a stereocenter in a cyclohexanone is achieved in a Michael addition see
    • For a related approach where facial selectivity with respect to a stereocenter in a cyclohexanone is achieved in a Michael addition see: Piers, E.; Keziere, R. J. Tetrahedron Lett. 1968, 583-586.
    • (1968) Tetrahedron Lett , pp. 583-586
    • Piers, E.1    Keziere, R.J.2
  • 180
    • 37049141049 scopus 로고
    • Odom and Pinder initially reported that nootkatone was the major product of this cyclization
    • Odom and Pinder initially reported that nootkatone was the major product of this cyclization: Odom, H. C; Pinder, A. R. Chem. Commun. 1969, 26-27.
    • (1969) Chem. Commun , pp. 26-27
    • Odom, H.C.1    Pinder, A.R.2
  • 203
    • 0023270476 scopus 로고
    • For a more recent cyclopropanation using a similar strategy see
    • For a more recent cyclopropanation using a similar strategy see: Hakam, K.; Thielmann, M.; Thielmann, T.; Winterfeldt, E. Tetrahedron 1987, 43, 2035-2044.
    • (1987) Tetrahedron , vol.43 , pp. 2035-2044
    • Hakam, K.1    Thielmann, M.2    Thielmann, T.3    Winterfeldt, E.4
  • 204
    • 33947464960 scopus 로고
    • For discussions of the solvent dependence on cis/trans selectivity and asymmetric induction in the Michael addition/cyclopropanations see
    • For discussions of the solvent dependence on cis/trans selectivity and asymmetric induction in the Michael addition/cyclopropanations see: McCoy, L. L. J. Am. Chem. Soc. 1958, 80, 6568-6572.
    • (1958) J. Am. Chem. Soc , vol.80 , pp. 6568-6572
    • McCoy, L.L.1
  • 208
    • 37049091403 scopus 로고
    • The structures of the major products in this paper are shown with the incorrect relative configurations (compare the structures in the paper to the ORTEP drawing from the X-ray crystal structure, which shows the correct relative configurations). Mulzer, J. personal communication
    • Mulzer, J.; Chucholowski, A.; Lammer, O.; Jibril, I.; Huttner, G. J. Chem. Soc, Chem. Commun. 1983, 869-71. The structures of the major products in this paper are shown with the incorrect relative configurations (compare the structures in the paper to the ORTEP drawing from the X-ray crystal structure, which shows the correct relative configurations). Mulzer, J. personal communication.
    • (1983) J. Chem. Soc, Chem. Commun , pp. 869-871
    • Mulzer, J.1    Chucholowski, A.2    Lammer, O.3    Jibril, I.4    Huttner, G.5
  • 210
    • 0001285938 scopus 로고
    • Ort, O. Org. Synth. 1987, 65, 203-214.
    • (1987) Org. Synth , vol.65 , pp. 203-214
    • Ort, O.1
  • 219
    • 84987360746 scopus 로고
    • A similar assignment for the stereochemistry of dienolates of allylic senecioates has been made on the basis of the subsequent Claisen rearrangements
    • A similar assignment for the stereochemistry of dienolates of allylic senecioates has been made on the basis of the subsequent Claisen rearrangements: Frater, G. Helv. Chim. Acta 1975, 58, 442-447.
    • (1975) Helv. Chim. Acta , vol.58 , pp. 442-447
    • Frater, G.1
  • 220
    • 0016777504 scopus 로고
    • There also has been a report that the deprotonation of methyl senecioate with LDA followed by trapping with trimethylsilyl chloride and heating results in a 1: 1 mixture of E and Z ketene acetals as a result of equilibration
    • Wilson, S. R.; Myers, R. S. J. Org. Chem. 1975, 40, 3309-3311. There also has been a report that the deprotonation of methyl senecioate with LDA followed by trapping with trimethylsilyl chloride and heating results in a 1: 1 mixture of E and Z ketene acetals as a result of equilibration:
    • (1975) J. Org. Chem , vol.40 , pp. 3309-3311
    • Wilson, S.R.1    Myers, R.S.2
  • 225
    • 0001126437 scopus 로고
    • For some further examples of the diastereoselective addition of enolates to nitroolefins in which the sense of the selectivity was not defined see, See also reference 113
    • For some further examples of the diastereoselective addition of enolates to nitroolefins in which the sense of the selectivity was not defined see: Seebach, D.; Calderri, G.; Kno-chel, P. Tetrahedron 1985, 41, 4861-4872. See also reference 113
    • (1985) Tetrahedron , vol.41 , pp. 4861-4872
    • Seebach, D.1    Calderri, G.2    Kno-chel, P.3
  • 226
    • 0001507197 scopus 로고
    • In this example, a,β-amino-α,(β-unsaturated nitro olefin was used as the acceptor. The products obtained are those from an additional elimination reaction and the diastereochemical preference for the Michael addition cannot be inferred
    • Fuji, K.; Node, M.; Nagasawa, H.; Naniwa, Y.; Terada, S. J. Am. Chem. Soc. 1986, 108, 3855-3856. In this example, a,β-amino-α,(β-unsaturated nitro olefin was used as the acceptor. The products obtained are those from an additional elimination reaction and the diastereochemical preference for the Michael addition cannot be inferred.
    • (1986) J. Am. Chem. Soc , vol.108 , pp. 3855-3856
    • Fuji, K.1    Node, M.2    Nagasawa, H.3    Naniwa, Y.4    Terada, S.5
  • 229
    • 0012054127 scopus 로고
    • For a similar study of the addition of cyanohydrins to conformationally fixed cyclohex-enones see
    • For a similar study of the addition of cyanohydrins to conformationally fixed cyclohex-enones see: Zervos, M.; Warski, L.; Seyden-Penne, J. Tetrahedron 1986, 42, 4963-4973.
    • (1986) Tetrahedron , vol.42 , pp. 4963-4973
    • Zervos, M.1    Warski, L.2    Seyden-Penne, J.3
  • 237
    • 0008909140 scopus 로고
    • For a related study of Lewis acid-promoted addition of silyl thioke-tene acetals to αβ-unsaturated ketones see:
    • For a related study of Lewis acid-promoted addition of silyl thioke-tene acetals to α,β-unsaturated ketones see: Goasdoue, C; Goasdoue, N.; Gaudemar, M. Tetrahedron Lett. 1984, 25, 537-540.
    • (1984) Tetrahedron Lett , vol.25 , pp. 537-540
    • Goasdoue, C.1    Goasdoue, N.2    Gaudemar, M.3
  • 241
    • 0000039570 scopus 로고
    • For additions performed with catalytic amounts of base see
    • For additions performed with catalytic amounts of base see: Stefanovsky, Y. N.; Viteva, L. Z. Monatsh. Chem. 1980, 111, 1287-1298.
    • (1980) Monatsh. Chem , vol.111 , pp. 1287-1298
    • Stefanovsky, Y.N.1    Viteva, L.Z.2
  • 243
    • 84986471166 scopus 로고
    • Chem. Abstr. 1972, 76, 24872L
    • (1972) Chem. Abstr , vol.76 , pp. 24872L
  • 246
    • 85083946267 scopus 로고
    • Chem. Abstr. 1982, 97, 215154s.
    • (1982) Chem. Abstr , vol.97 , pp. 215154s
  • 248
    • 84986495003 scopus 로고
    • Chem. Abstr. 1971, 75, 88270v.
    • (1971) Chem. Abstr , vol.75 , pp. 88270v
  • 252
    • 0039497736 scopus 로고
    • For a discussion of the use of metallated imines and hydrazones see
    • For a discussion of the use of metallated imines and hydrazones see: Hickmott, P. W. Tetrahedron 1982, 38, 3363-3446.
    • (1982) Tetrahedron , vol.38 , pp. 3363-3446
    • Hickmott, P.W.1
  • 253
    • 85021527564 scopus 로고
    • For a discussion of the stereochemical aspects of hydrazone and imine alkylations (both with alkyl halides and activated olefins) see, Morrison, J. D., Ed.; Academic: New York, Chapter 9
    • For a discussion of the stereochemical aspects of hydrazone and imine alkylations (both with alkyl halides and activated olefins) see: Bergbreiter, D. E.; Newcomb, M. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, Vol. 2, 1983, Chapter 9.
    • (1983) In Asymmetric Synthesis; , vol.2
    • Bergbreiter, D.E.1    Newcomb, M.2
  • 254
    • 0001178719 scopus 로고
    • For a discussion of the deprotonation and electrophilic substitution of hydrazones (including SAMP and RAMP hydrazones), along with possibilities for the source of asymmetric induction seen in these reactions see
    • For a discussion of the deprotonation and electrophilic substitution of hydrazones (including SAMP and RAMP hydrazones), along with possibilities for the source of asymmetric induction seen in these reactions see: Davenport, K. G.; Eichenauer, H.; Enders, D.; New-comb, M.; Bergbreiter, D. E. J. Am. Chem. Soc. 1979, 101, 5654-5659.
    • (1979) J. Am. Chem. Soc , vol.101 , pp. 5654-5659
    • Davenport, K.G.1    Eichenauer, H.2    Enders, D.3    New-comb, M.4    Bergbreiter, D.E.5
  • 257
    • 0000616585 scopus 로고
    • Angew. Chem. 1963, 75, 978-979.
    • (1963) Angew. Chem , vol.75 , pp. 978-979
  • 262
  • 269
    • 0000292389 scopus 로고
    • Angew. Chem. 1981, 93, 793-795.
    • (1981) Angew. Chem , vol.93 , pp. 793-795
  • 271
    • 85080365841 scopus 로고
    • Angew. Chem. 1987, 99, 480-482.
    • (1987) Angew. Chem , vol.99 , pp. 480-482
  • 272
    • 84985287451 scopus 로고
    • For a recent example of the addition of 90.2 to enoates see
    • For a recent example of the addition of 90.2 to enoates see: Schöllkopf, U.; Schröder, J. Liebigs Ann. Chem. 1988, 87-92.
    • (1988) Liebigs Ann. Chem , pp. 87-92
    • Schöllkopf, U.1    Schröder, J.2
  • 277
    • 0037692931 scopus 로고
    • (a)deJeso, B.; Pommier, J.-C. Tetrahedron Lett. 1980,2', 4511-4514.
    • (1980) Tetrahedron Lett , vol.2 , pp. 4511-4514
  • 280
    • 85080456017 scopus 로고    scopus 로고
    • We have also observed low levels of diastereoselection for the Michael additions, unpublished results
    • We have also observed low levels of diastereoselection for the Michael additions: Oare, D. A.; Heathcock, C. H. unpublished results.
    • Oare, D.A.1    Heathcock, C.H.2
  • 293
    • 0007066231 scopus 로고
    • Angew. Chem. 1976, 88, 389-401.
    • (1976) Angew. Chem , vol.88 , pp. 389-401
  • 295
    • 85080366066 scopus 로고
    • Zh. Org. Khim. 1983, 19, 661-662.
    • (1983) Zh. Org. Khim , vol.19 , pp. 661-662
  • 297
    • 0009197659 scopus 로고
    • and references therein
    • Zh. Org. Khim. 1983, 19, 941-951 and references therein.
    • (1983) Zh. Org. Khim , vol.19 , pp. 941-951
  • 299
    • 85083946275 scopus 로고
    • Chem. Abstr. 1984,101, 170928e.
    • (1984) Chem. Abstr , vol.101 , pp. 170928e
  • 305
    • 0001696111 scopus 로고
    • and references therein
    • Hirama, M. Tetrahedron Lett. 1981, 22, 1905-1908 and references therein.
    • (1981) Tetrahedron Lett , vol.22 , pp. 1905-1908
    • Hirama, M.1
  • 314
    • 85080381578 scopus 로고
    • Zh. Obshch. Khim. 1983, 52, 2651-2652.
    • (1983) Zh. Obshch. Khim , vol.52 , pp. 2651-2652
  • 321
    • 0344361923 scopus 로고
    • For a discussion of Baldwin's rules for ring closure see
    • For a discussion of Baldwin's rules for ring closure see: Baldwin, J. E. J. Chem. Soc, Chem. Commun. 1976, 734-736.
    • (1976) J. Chem. Soc, Chem. Commun , pp. 734-736
    • Baldwin, J.E.1
  • 327
    • 37049098529 scopus 로고
    • For a discussion of Baldwin's rule's with respect to intramolecular reaction of enolates see
    • For a discussion of Baldwin's rule's with respect to intramolecular reaction of enolates see: Baldwin, J. E.; Kruse, L. I. J. Chem. Soc, Chem. Commun. 1977, 233-235.
    • (1977) Chem. Soc, Chem. Commun , pp. 233-235
    • Baldwin, J.E.1    Kruse, L.I.J.2
  • 332
    • 0001624349 scopus 로고
    • and references therein
    • Jackman, L. M.; Lange, B. C. Tetrahedron 1977, 33, 2737-2769, and references therein.
    • (1977) Tetrahedron , vol.33 , pp. 2737-2769
    • Jackman, L.M.1    Lange, B.C.2
  • 335
    • 0021235736 scopus 로고
    • For a similar approach where the base-promoted cyclization products underwent further condensation see
    • For a similar approach where the base-promoted cyclization products underwent further condensation see: Massiot, G.; Mulamba, T.J. Chem. Soc, Chem. Commun. 1984, 715-716.
    • (1984) Chem. Soc, Chem. Commun , pp. 715-716
    • Massiot, G.1    Mulamba, T.J.2
  • 336
    • 0023201660 scopus 로고
    • For recent applications of intramolecular Michael additions towards the synthesis of forskolin see
    • For recent applications of intramolecular Michael additions towards the synthesis of forskolin see: Koft, E. R.; Kotnis, A. S.; Broadbent, T. A. Tetrahedron Lett. 1987, 28, 2799-2800.
    • (1987) Tetrahedron Lett , vol.28 , pp. 2799-2800
    • Koft, E.R.1    Kotnis, A.S.2    Broadbent, T.A.3
  • 356
    • 85082709521 scopus 로고
    • For a recent review of this subject see
    • For a recent review of this subject see: Schinzer, D. Synthesis 1988, 263-273.
    • (1988) Synthesis , pp. 263-273
    • Schinzer, D.1
  • 365
    • 37049134917 scopus 로고
    • Similar observations about the stepwise nature of the reaction have been made by Ban and coworkers
    • Similar observations about the stepwise nature of the reaction have been made by Ban and coworkers: Ohnuma, T.; Oishi, T.; Ban, Y. J. Chem. Soc, Chem. Commun. 1973, 301-302.
    • (1973) Chem. Soc, Chem. Commun , pp. 301-302
    • Ohnuma, T.1    Oishi, T.2    Ban, Y.J.3
  • 366
    • 49349138797 scopus 로고
    • For an application of this technology towards the synthesis of natural products see
    • White, K. B.; Reusch, W. Tetrahedron 1978, 34, 2439-2443. For an application of this technology towards the synthesis of natural products see:
    • (1978) Tetrahedron , vol.34 , pp. 2439-2443
    • White, K.B.1    Reusch, W.2
  • 368
    • 0001145704 scopus 로고
    • For another example of isolation of mono-addition products see, Although the possibility of stereochemical differentiation occurs with the substrates studied in this reference, no mention of the stereochemical outcome was given
    • For another example of isolation of mono-addition products see: Hagiwara, H.; Naka-yama, K.; Uda, H. Bull. Chem. Soc. Jpn. 1975,48, 3769-3770. Although the possibility of stereochemical differentiation occurs with the substrates studied in this reference, no mention of the stereochemical outcome was given.
    • (1975) Bull. Chem. Soc. Jpn , vol.48 , pp. 3769-3770
    • Hagiwara, H.1    Naka-yama, K.2    Uda, H.3
  • 370
    • 37049135848 scopus 로고
    • For some additional examples of formal tandem Michael additions where no stereochemical insight can be gained see
    • For some additional examples of formal tandem Michael additions where no stereochemical insight can be gained see: Bellamy, A. J. J. Chem. Soc. (B) 1969, 449-455.
    • (1969) Chem. Soc. (B) , pp. 449-455
    • Bellamy, A.J.J.1
  • 374
    • 85080428605 scopus 로고
    • Zh. Obshch. Khim. 1964, 34, 3205-3212.
    • (1964) Zh. Obshch. Khim , vol.34 , pp. 3205-3212
  • 378
    • 0010979883 scopus 로고
    • For a closely related example where the subsequent alkylation strongly supports the initial generation of the endo product see
    • Angew. Chem. 1982, 94, 639. For a closely related example where the subsequent alkylation strongly supports the initial generation of the endo product see:
    • (1982) Angew. Chem , vol.94 , pp. 639
  • 392
    • 0008892890 scopus 로고
    • For closely related application to the synthesis of atisiran-15-one see:
    • For closely related application to the synthesis of atisiran-15-one see: Ihara, M.; Toyota, M.; Fukumoto, K.; Kametani, T. Tetrahedron Lett. 1985, 26, 1537-1540.
    • (1985) Tetrahedron Lett , vol.26 , pp. 1537-1540
    • Ihara, M.1    Toyota, M.2    Fukumoto, K.3    Kametani, T.4
  • 404
    • 37049068342 scopus 로고
    • For a discussion of open-extended versus closed chelated transition states for the addition of phenyllithium to α,β-unsaturated ketones see
    • For a discussion of open-extended versus closed chelated transition states for the addition of phenyllithium to α,β-unsaturated ketones see: Ignatova-Avramova, E. P.; Pojarlieff, I. G.J. Chem. Soc.. Perkin Trans. 2 1986, 69-73.
    • (1986) J. Chem. Soc.. Perkin Trans. 2 , pp. 69-73
    • Ignatova-Avramova, E.P.1    Pojarlieff, I.G.2
  • 412
    • 0003594275 scopus 로고
    • Allinger, N. L.; Eliel, E. L.; Wilen, S. H. Eds.; Wiley: New York, Chapter 1
    • Evans, D. A.; Nelson, J. V.; Taber, T. R. Topics in Stereochemistry; Allinger, N. L.; Eliel, E. L.; Wilen, S. H. Eds.; Wiley: New York, 1982; Vol. 13, Chapter 1.
    • (1982) Topics in Stereochemistry; , vol.13
    • Evans, D.A.1    Nelson, J.V.2    Taber, T.R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.