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(b) A most recent example using 1.2 equivalents of a strained chiral silane reagent as Lewis acid: Shirakawa, S.; Berger, R.; Leighton, J. L. J. Am. Chem. Soc. 2005, 127, 2858.
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1042276935
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(i) Levkovskaya, G. G.; Rudyakova, E. V.; Rozentsveig, I. B.; Mirskova, A. N.; Albanov, A. I. Zh. Org. Khim. 2000, 36, 1378.
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32
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0037244819
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Reviews for Mannich-type reaction involving glyoxylate imines, see: (a) Taggi, A. E.; Hafez, A. M.; Leckta, T. Acc. Chem. Res. 2003, 36, 10.
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Taggi, A.E.1
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35
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2342570203
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For examples for chiral Brønsted acid catalysis in Mannich type or aza-Friedel-Crafts reactions, see: (a) Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem. Int. Ed. 2004, 43, 1566.
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Akiyama, T.1
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37
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38
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0033617391
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4 as a weak Lewis acid catalyst was excluded: (a) Kisanga, P.; McLeod, D.; D'Sa, B.; Verkade, J. J. Org. Chem. 1999, 64, 3090.
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Kisanga, P.1
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40
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0037017031
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Commercially available reagent: Fluke #50705, Lancaster #19207 and TCI#G0264. Control experiments gave similar results using ethyl glyoxylate (or its hydrate) prepared according to the literature: (a) Bailey, P. D.; Smith, P. D.; Pederson, F.; Clegg, W.; Rosair, G. M.; Teat, S. J. Tetrahedron Lett. 2002, 43, 1067.
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Bailey, P.D.1
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Teat, S.J.6
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42
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33645490271
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note
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2H, MsOH, etc.), the yields were not improved and the diastereoselectivities were deteriorated in the following study.
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43
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33645484206
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note
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2 (5 atm), EtOH, r.t., 24 h, 41% yield of (+)-ethyl (3-indolyl)glycinate (21).
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