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For BMDMSCl-related derivatives, see
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D. E. Kaelin Jr.. S. M. Sparks, H. R. Plake, S. F. Martin. J. Am. Chem. Soc. 2003, 125, 12994-12995. For BMDMSCl-related derivatives, see:
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(2003)
J. Am. Chem. Soc
, vol.125
, pp. 12994-12995
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Kaelin Jr., D.E.1
Sparks, S.M.2
Plake, H.R.3
Martin, S.F.4
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81
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63849290684
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W. Simmler, Chem. Ber. 1961, 94, 1585-1591;
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(1961)
Chem. Ber
, vol.94
, pp. 1585-1591
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Simmler, W.1
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83
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63849219222
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2O) test reaction run in parallel under the same double deprotonation conditions unambiguously led to the formation of 3-(Z)-deuterio-N-phenylallylamine as the unique product. The incorporation of deuterium reached 91% and was totally regio- and Z-stereoselective.
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2O) test reaction run in parallel under the same double deprotonation conditions unambiguously led to the formation of 3-(Z)-deuterio-N-phenylallylamine as the unique product. The incorporation of deuterium reached 91% and was totally regio- and Z-stereoselective.
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84
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63849323817
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N-Phenyl-3,3-dimethyl-l-aza-3-silacyclohex-4-ene (5, To a stirred solution of N-phenylallyla.mine (4, 2.9 mI, 20 mmol, 1.0 equiv, in freshly distilled Et2O(50 mI, was added dropwise freshly titrated/BuLi (1.48 m, 27 mL, 40 mmol, 2.0 equiv, at -78 °C After the addition, the reaction mixture was slowly warmed to 0 °C, after which BMDMSC1 (3.4 mL, 24 mmol, 1.2 equiv, was added dropwise, and the reaction mixture was stirred for 1 h at room temperature. The resulting solution was then submitted to an Et2O/H2O extraction. The combined organic layers were washed with NaCl, dried with anhydrous MgSO4, filtered and evaporated in vacuo. Purification was achieved by flash column chromatography on silica gel (PE/Et2O gradient, A pale yellow oil was obtained. Yield: 2.89 g (70, 1H NMR (CDC13, 400 MHz, δ, 7.26 (m, 2 H, m-Ph, 6.97 (m, 2 H, o-Ph, 6.82 m, 1 II, p
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17NSi: C 70.88, H 8.43, N 6.89; found: C 70.82, H 8.53, N, 6.95.
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85
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0033101277
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For a review on heteroatom-stabilized allyl anions, see
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For a review on heteroatom-stabilized allyl anions, see: A. R. Katritzky, M. Piffl, IT. Lang, E. Anders, Chem. Rev. 1999, 99, 665-772.
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(1999)
Chem. Rev
, vol.99
, pp. 665-772
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Katritzky, A.R.1
Piffl, M.2
Lang, I.T.3
Anders, E.4
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86
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0029943738
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The deprotonation was anticipated to occur regioselectively at the allylic position and to give rise to anion E. For a study on the regioselectivity of the deprotonation of similar systems, see: S. M. Sieburth, J. J. Somers, Tetrahedron 1996, 52, 5683-5690
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The deprotonation was anticipated to occur regioselectively at the allylic position and to give rise to anion E. For a study on the regioselectivity of the deprotonation of similar systems, see: S. M. Sieburth, J. J. Somers, Tetrahedron 1996, 52, 5683-5690.
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87
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63849178416
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The direct dropwise addition of methyl chloroformate to anion E resulted in a complex mixture in which neither starting material 5 nor the expected a-aminoester 9 were to be found. Undesired subsequent side reactions involving compound 9 and anion E are suspected to have occurred.
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The direct dropwise addition of methyl chloroformate to anion E resulted in a complex mixture in which neither starting material 5 nor the expected a-aminoester 9 were to be found. Undesired subsequent side reactions involving compound 9 and anion E are suspected to have occurred.
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88
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0024335768
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Pipecolic acid is present in certain human physiologic fluids. It does not possess a well-defined biological activity, but plays a role in the central nervous system: a M. C. Gutierrez, B. A. Delgado-Coello, Neurochem. Res. 1989, 14, 405-408;
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Pipecolic acid is present in certain human physiologic fluids. It does not possess a well-defined biological activity, but plays a role in the central nervous system: a) M. C. Gutierrez, B. A. Delgado-Coello, Neurochem. Res. 1989, 14, 405-408;
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89
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0037908895
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T. Fujita, M. Fujita. T. Kodama, T. Hada, K. Higashino, Annals Nutrition Metabolism 2003, 47, 165-169. See also:
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T. Fujita, M. Fujita. T. Kodama, T. Hada, K. Higashino, Annals Nutrition Metabolism 2003, 47, 165-169. See also:
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90
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0032783850
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and references cited therein
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F. P. J. T. Rutjes, J. J. N. Veerman, W. J. N. Meester, H. Hiemstra, H. E. Schoernaker, Eur. J. Org. Chem. 1999, 1127-1135 and references cited therein.
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(1999)
Eur. J. Org. Chem
, pp. 1127-1135
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Rutjes, F.P.J.T.1
Veerman, J.J.N.2
Meester, W.J.N.3
Hiemstra, H.4
Schoernaker, H.E.5
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91
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0002721151
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a) R. J. P. Corriu, J. Masse, D. Sarnate, J. Organomet. Chem. 1975, 93, 71-80;
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(1975)
J. Organomet. Chem
, vol.93
, pp. 71-80
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Corriu, R.J.P.1
Masse, J.2
Sarnate, D.3
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92
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0000057020
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R. F. Horvath, T. H. Chan. J. Org. Chem. 1987, 52, 4489-4494. See also:
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R. F. Horvath, T. H. Chan. J. Org. Chem. 1987, 52, 4489-4494. See also:
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94
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63849168732
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[11] for transmetallation with titanium(IV), and references cited therein.
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[11] for transmetallation with titanium(IV), and references cited therein.
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