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Reviews: Hoppe, D.; Hintze, F.; Tebben, P.; Paetow, M.; Ahrens, H.; Schwerdtfeger, J.; Sommerfeld, P.; Haller, J.; Guarniere, W.; Kolczewski, S.; Hense, T.; Hoppe, I. Pure Appl. Chem. 1994, 66, 1479. Hoppe, D.; Ahrens, H.; Guarnieri, W.; Helmke, H.; Kolczewski, S. Pure Appl. Chem. 1996, 68, 613.
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Reviews: Hoppe, D.; Hintze, F.; Tebben, P.; Paetow, M.; Ahrens, H.; Schwerdtfeger, J.; Sommerfeld, P.; Haller, J.; Guarniere, W.; Kolczewski, S.; Hense, T.; Hoppe, I. Pure Appl. Chem. 1994, 66, 1479. Hoppe, D.; Ahrens, H.; Guarnieri, W.; Helmke, H.; Kolczewski, S. Pure Appl. Chem. 1996, 68, 613.
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Guarnieri, W.; Grehl, M.; Hoppe, D. Angew. Chem. 1994, 106, 1815; Angew. Chem. Int. Ed. Engl. 1994, 33, 1734.
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Guarnieri, W.1
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0009529363
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The deuteriated compounds 10a and 101, in a stricter sense, do not match with the Masamune convention. Masamune, S.; Ali, S.A.; Snitman, D.L.; Garvey, D.S. Angew. Chem. 1980, 92, 573; Angew. Chem. Int. Ed. Eng. 1980, 19, 557.
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Ali, S.A.2
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84985553225
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The deuteriated compounds 10a and 101, in a stricter sense, do not match with the Masamune convention. Masamune, S.; Ali, S.A.; Snitman, D.L.; Garvey, D.S. Angew. Chem. 1980, 92, 573; Angew. Chem. Int. Ed. Eng. 1980, 19, 557.
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O'Donnell, M.J.; Polt, R.L. J. Org. Chem. 1982, 47, 2663. Peterson, M.A.; Polt, R. J. Org. Chem. 1993, 58, 4309. Szabo, L.; Li, Y.; Polt, R. Tetrahedron Lett. 1991, 32, 585.
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8044224005
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note
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The prefix ent means that the addressed compound is the mirror image of its enantiomer shown in the formula scheme.
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17
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3543013475
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Hagemann, H., Klamann, D., Eds.; Thieme: Stuttgart
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Review: Raßhofer, W. In Houben-Weyl, 4th ed., Vol. E14a/2; Hagemann, H., Klamann, D., Eds.; Thieme: Stuttgart, 1990; pp 595-679.
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Kolczewski, S.1
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33749124991
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For the problems arising from double stereoselection in (-)-sparteine-mediated deprotonations, see also: Haller, J.; Hense, T.; Hoppe, D. Liebigs Ann. Chem. 1996, 489.
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Haller, J.1
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Gilman, H.; Kirby, J.E.; Kinney, C.R. J. Am. Chem. Soc. 1929, 51, 2252.
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8044233689
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note
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The deprotonation reaction with sec-butyllithium/TMEDA (MeOD as electrophile) yielded only 5% of an EjZ mixture of the sec-butyl-substituted adduct and 15% of the 1-deuteriated carbamate (> 95% D). The reaction with sec-butyllithium/(-)-sparteine was even more complicated and gave 35% of the sec-butyl-substituted adduct and in addition a mixture of the 3-, the 1-deuteriated carbamate and 14 (18%, 9:29:62).
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