One-pot Synthesis of Lactams Using Domino Reactions: Combination of Schmidt Reaction with Sakuri and Aldol Reaction

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Issue Date
2009-10-16Author
Huh, Chan Woo
Somal, Gagandeep K.
Katz, Christopher E.
Pei, Huanxing
Zeng, Yibin
Douglas, Justin T.
Aubé, Jeffrey
Publisher
American Chemical Society
Type
Article
Article Version
Scholarly/refereed, author accepted manuscript
Rights
This document is the Accepted Manuscript version of a Published Work that appeared in final form in the Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/jo901843w.
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Show full item recordAbstract
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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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
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