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(a) Schmidt, U.; Meyer, R.; Leitenberger, V.; Griesser, H.; Lieberknecht, A. Synthesis 1992, 1025.
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Schmidt, U.1
Meyer, R.2
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Lieberknecht, A.5
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(b) Schmidt, U.; Leitenberger, V.; Griesser, H.; Schmidt, J.; Meyer, R. Synthesis 1992, 1248.
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Synthesis
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Schmidt, U.1
Leitenberger, V.2
Griesser, H.3
Schmidt, J.4
Meyer, R.5
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3
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(c) Bois-Choussy, M.; Cristau, P.; Zhu, J. Angew. Chem. Int. Ed. 2003, 42, 4238.
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Zhu, J.3
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5
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0141869035
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David, O.; Meester, W. J. N.; Bieräugel, H.; Schoemaker, H. E.; Hiemstra, H.; van Maarseveen, J. H. Angew. Chem. Int. Ed. 2003, 42, 4373.
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Meester, W.J.N.2
Bieräugel, H.3
Schoemaker, H.E.4
Hiemstra, H.5
Van Maarseveen, J.H.6
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7
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(b) Lin, F. L.; Hoyt, H. M.; van Halbeek, H.; Bergman, R. G.; Bertozzi, C. R. J. Am. Chem. Soc. 2005, 127, 2686.
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Lin, F.L.1
Hoyt, H.M.2
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Bergman, R.G.4
Bertozzi, C.R.5
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8
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0037067343
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(c) Soellner, M. B.; Nilsson, B. L.; Raines, R. T. J. Org. Chem. 2002, 67, 4993.
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J. Org. Chem.
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Soellner, M.B.1
Nilsson, B.L.2
Raines, R.T.3
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9
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10044248464
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He, Y.; Hinklin, R. J.; Chang, J.; Kiessling, L. L. Org. Lett. 2004, 6, 4479.
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Org. Lett.
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He, Y.1
Hinklin, R.J.2
Chang, J.3
Kiessling, L.L.4
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10
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0032564850
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Imamoto, T.; Watanabe, J.; Wada, Y.; Masuda, H.; Yamada, H.; Tsuruta, H.; Matsukawa, S.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 1635.
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Imamoto, T.1
Watanabe, J.2
Wada, Y.3
Masuda, H.4
Yamada, H.5
Tsuruta, H.6
Matsukawa, S.7
Yamaguchi, K.8
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11
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0035179655
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For a similar approach using phenyl disulfide for the introduction of sulfur, see: Sugama, H.; Saito, H.; Danjo, H.; Imamoto, T. Synthesis 2001, 2348.
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Synthesis
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Sugama, H.1
Saito, H.2
Danjo, H.3
Imamoto, T.4
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12
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33645759726
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note
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3): δ = 31.41 (q, J = 59.0 Hz).
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13
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33645784577
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note
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Recrystallization to increase the ee was impossible because the product is a pasty solid.
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14
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0034733113
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The absolute configuration of 3 was determined by comparison with the known (R)-tert-butyl(hydroxymethyl) methylphosphine borane. The alcohol was converted to the thioacetate in two steps followed by acetyl group removal to give the chiral thiol, see: Nagata, K.; Matsukawa, S.; Imamoto, T. J. Org. Chem. 2000, 65, 4185.
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J. Org. Chem.
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, pp. 4185
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Nagata, K.1
Matsukawa, S.2
Imamoto, T.3
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17
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33645771449
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note
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The boronic acid component for the Suzuki coupling from 7 was prepared by lithium-halogen exchange with n-BuLi and treatment with triethyl borate.
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18
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3042654141
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Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem. Int. Ed. 2004, 43, 1871.
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(2004)
Angew. Chem. Int. Ed.
, vol.43
, pp. 1871
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Walker, S.D.1
Barder, T.E.2
Martinelli, J.R.3
Buchwald, S.L.4
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19
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0035826370
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ω-Azido acids were obtained from ω-amino acids by a diazotransfer reaction: Lundquist, J. T.; Pelletier, J. C. Org. Lett. 2001, 3, 781.
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(2001)
Org. Lett.
, vol.3
, pp. 781
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Lundquist, J.T.1
Pelletier, J.C.2
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20
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0010319662
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( 14) For an extensive review on applications of borane-protected phosphines see: Brunel, J. M.; Faure, B.; Maffei, M. Coord. Chem. Rev. 1998, 180, 665.
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(1998)
Coord. Chem. Rev.
, vol.180
, pp. 665
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Brunel, J.M.1
Faure, B.2
Maffei, M.3
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21
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33645763202
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note
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13C NMR (100 MHz, MeOD): δ = 175.9, 170.9, 143.1, 143.0, 140.8, 139.7, 135.7, 134.2, 133.9, 132.2, 131.6, 130.7, 128.2, 127.5, 43.8, 41.2, 37.3, 30.5, 29.1, 27.4, 30.0, 19.6.
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22
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33645793502
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note
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Attempts to produce 17c via lactamization of the pentafluorophenyl ester analogue of 12c using an aza-Wittig reaction failed.
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-
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23
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33645753501
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note
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The atropenantiomers were separated by analytical HPLC analysis using a chiral Daicel OD-H column with heptane-i-PrOH (98:2) as the eluent.
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24
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33645791242
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Eshdat, L.; Shabtai, E.; Saleh, S. A.; Sternfeld, T.; Saito, M.; Okamoto, Y.; Rabinovitz, M. J. Org. Chem. 1999, 64, 353.
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J. Org. Chem.
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Eshdat, L.1
Shabtai, E.2
Saleh, S.A.3
Sternfeld, T.4
Saito, M.5
Okamoto, Y.6
Rabinovitz, M.7
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25
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0042324377
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For the first example of atropenantioselective macrocyclizations see: Islas-Gonzalez, G.; Bois-Choussy, M.; Zhu, J. Org. Biomol. Chem. 2003, 1, 30.
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(2003)
Org. Biomol. Chem.
, vol.1
, pp. 30
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Islas-Gonzalez, G.1
Bois-Choussy, M.2
Zhu, J.3
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