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One-pot Synthesis of Lactams Using Domino Reactions: Combination of Schmidt Reaction with Sakuri and Aldol Reaction
Huh, Chan Woo Somal, Gagandeep K. Katz, Christopher E. Pei, Huanxing Zeng, Yibin Douglas, Justin T. Aubé, Jeffrey
Huh, Chan Woo
Somal, Gagandeep K.
Katz, Christopher E.
Pei, Huanxing
Zeng, Yibin
Douglas, Justin T.
Aubé, Jeffrey
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Abstract
A series of domino reactions in which the intramolecular Schmidt reaction is combined with either a Sakurai reaction, an aldol reaction, or both is reported. The Sakurai reaction of an allylsilane with an azido-containing enone under Lewis acidic conditions followed by protonation of the resulting titanium enolate species allowed for a subsequent intramolecular Schmidt reaction. Alternatively, the intermediate titanium enolate could undergo an aldol reaction, followed by the intramolecular Schmidt reaction to form lactam products with multiple stereogenic centers. The stereochemical features of the titanium enolate aldol reaction with several 3-azidoaldehyde substrates during this domino process is discussed.
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Date
2009-10-16
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American Chemical Society
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Keywords
Schmidt reaction, Lactam synthesis, Azides, Domino reaction, Sakurai reaction, Stereoselective aldol reaction, Titanium enolate, GOESY
Citation
Huh, C. W., Somal, G. K., Katz, C. E., Pei, H., Zeng, Y., Douglas, J. T., & Aubé, J. (2009). One-pot Synthesis of Lactams Using Domino Reactions: Combination of Schmidt Reaction with Sakurai and Aldol Reactions. The Journal of Organic Chemistry, 74(20), 7618–7626. http://doi.org/10.1021/jo901843w