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0001532596
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Other references for synthesis of chiral-π-allylpalladium complex complexes, see: (b) Rosset, J.-M.; Glenn, M. P.; Cotton, J. D.; Willis, A. C.; Kennard, C. H. L.; Byriel, K. A.; Riches, B. H.; Kitching, W. Organometallics 1998, 17, 1968.
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31
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0025309685
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Olefin 7 (E:Z = 1:1) was prepared starting from (1S)-(-)-β-pinene available in Aldrich Chemical Co. in 97% ee. Though (IR)-(+)-nopinone (90% ee) is also available, we preferred to prepare it from (1S)-(-)-β-pinene by ozonolysis of exocyclic double bond. Further Wittig reaction with ethyltriphenylphosphonium bromide and BuOK gave 7 (E:Z = 1:1) [see: Brown, H. C.; Weissman, S. A.; Perumal, P. T.; Dhokte, U. P. J. Org. Chem. 1990, 55, 1217].
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32
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0242478548
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note
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The solvents tried were 2-butanone, propionitrile, 2-propanol, and diisopropyl ether. Among all, propionitrile gave best upgradation ratio of 2a: 2b and recovery of catalyst during recrystalization. Though the catalyst is not freely soluble in propionitrile, warming to 90 °C gave clear solution. Higher temperatures or boiling should be avoided to prevent catalyst decomposition.
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33
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0242646942
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note
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1H NMR of 2a:2b = 1.3:1, 100:1, and >400:1.
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34
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0242478547
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note
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1H NMR spectrum available the ratio of the catalyst 2a:2b was 20:1. To the best of our knowledge, this is the first report of preparation of the catalyst 2a and separated from its undesired stereoisomer with a ratio of 2a:2b >400:1.
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35
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0242562342
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note
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3). See the Supporting Information for more details.
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36
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0242395115
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note
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3CN was added for better solubilization of stannane byproducts.
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37
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0242562343
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note
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Details for each compound are giving in the Supporting Information.
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38
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0000561215
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(a) van der Sluis, M.; Dalmolen, J.; de Lange, B.; Kaptein, B.; Kellogg, R. M.; Broxterman, Q. B. Org. Lett. 2001, 3, 3943.
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Broxterman, Q.B.6
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39
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0029839451
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(b) Cvetovich, R. J.; Chartrain, M.; Hartner, F. W., Jr.; Roberge, C.; Amato, J. S.; Grabowski, E. J. J. J. Org. Chem. 1996, 61, 6575.
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Grabowski, E.J.J.6
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40
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0242562341
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note
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However, the enhancement of enantioselectivity by water is not clear. Formation of pentacoordinate Si is known, see reference (2), probably similar is the case with stannane.
-
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-
-
41
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0242646941
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note
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A similar explanation is given by Hou, see: ref (2c).
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