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Stetter, H.1
Kuhlmann, H.2
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9
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0018422536
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Tethering the aldehyde to the conjugate acceptor (intramolecular reaction) or significant excess of aldehyde can alleviate the problem of benzoin formation in the Stetter reaction, see: (a) Trost, B. M.; Shuey, C. D.; Dininno, F.; McElvain, S. S. J. Am. Chem. Soc. 1979, 101, 1284-1285.
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(b) Degl'Innocenti, A.; Ricci, A.; Mordini, A.; Reginato, G.; Colotta, V. Gazz. Chim. Ital. 1987, 117, 645-648.
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Degl'Innocenti, A.1
Ricci, A.2
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Colotta, V.5
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19
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37049104721
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(c) Degl'Innocenti, A.; Pike, S.; Walton, D. R. M.; Seconi, G.; Ricci, A.; Fiorenza, M. J. Chem. Soc., Chem. Commun. 1980, 1201-1202.
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Degl'Innocenti, A.1
Pike, S.2
Walton, D.R.M.3
Seconi, G.4
Ricci, A.5
Fiorenza, M.6
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20
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0038001592
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(d) Xin, L. H.; Johnson, J. S. Angew. Chem., Int. Ed. 2003, 42, 2534-2536.
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21
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0002237394
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and references therein
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(a) Brook, A. G. Acc. Chem. Res. 1974, 7, 77-84 and references therein.
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(b) Moser, W. H. Tetrahedron 2001, 57, 2065-2084.
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Moser, W.H.1
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23
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1542349851
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note
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Control experiments omitting either DBU (1,8-diazoabicyclo-[5.4.0]-undecane) or 4 resulted in no product formation.
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24
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1542349852
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note
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Thiazolium salts such as 3-benzyl-4,5-dimethylthiazolium bromide afford no product when exogenous alcohols were omitted from the reaction.
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25
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1542379644
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note
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The use of benzoyltrimethylsilane (1a) for these reactions results in significantly reduced conversion. This observation is under investigation.
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26
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0030569373
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For mechanistic investigations of thiazolium salts as catalysts, see: (a) Breslow, R.; Schmuck, C. Tetrahedron Lett. 1996, 37, 8241-8242.
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(1996)
Tetrahedron Lett.
, vol.37
, pp. 8241-8242
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Breslow, R.1
Schmuck, C.2
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27
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0000060093
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and references therein
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(b) Chen, Y. T.; Barletta, G. L.; Haghjoo, K.; Cheng, J. T.; Jordan, F. J. Org. Chem. 1994, 59, 7714-7722 and references therein.
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(1994)
J. Org. Chem.
, vol.59
, pp. 7714-7722
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Chen, Y.T.1
Barletta, G.L.2
Haghjoo, K.3
Cheng, J.T.4
Jordan, F.5
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28
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1542349853
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note
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The use of 3-octanol in the reaction affords 3-trimethylsilyloxyoctane (observed by gas chromatography), thus implicating the alcohol as the ultimate silyl acceptor. See Supporting Information for details.
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29
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1542319803
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note
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Replacing la with PhCHO affords mainly benzoin and only 20-30% of 5.
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