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dc.contributor.authorHuh, Chan Woo
dc.contributor.authorSomal, Gagandeep K.
dc.contributor.authorKatz, Christopher E.
dc.contributor.authorPei, Huanxing
dc.contributor.authorZeng, Yibin
dc.contributor.authorDouglas, Justin T.
dc.contributor.authorAubé, Jeffrey
dc.identifier.citationHuh, 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.
dc.description.abstractA 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.en_US
dc.publisherAmerican Chemical Societyen_US
dc.rightsThis 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
dc.subjectSchmidt reactionen_US
dc.subjectLactam synthesisen_US
dc.subjectDomino reactionen_US
dc.subjectSakurai reactionen_US
dc.subjectStereoselective aldol reactionen_US
dc.subjectTitanium enolateen_US
dc.titleOne-pot Synthesis of Lactams Using Domino Reactions: Combination of Schmidt Reaction with Sakuri and Aldol Reactionen_US
kusw.kuauthorHuh, Chan Woo
kusw.kuauthorSomal, Gagandeep K.
kusw.kuauthorKatz, Christopher E.
kusw.kuauthorPei, Huanxing
kusw.kuauthorZeng, Yibin
kusw.kuauthorDouglas, Justin T.
kusw.kuauthorAubé, Jeffrey
kusw.kudepartmentMedicinal Chemistryen_US
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kusw.oaversionScholarly/refereed, author accepted manuscripten_US
kusw.oapolicyThis item meets KU Open Access policy criteria.en_US

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