dc.contributor.author | Huh, Chan Woo | |
dc.contributor.author | Somal, Gagandeep K. | |
dc.contributor.author | Katz, Christopher E. | |
dc.contributor.author | Pei, Huanxing | |
dc.contributor.author | Zeng, Yibin | |
dc.contributor.author | Douglas, Justin T. | |
dc.contributor.author | Aubé, Jeffrey | |
dc.date.accessioned | 2017-04-12T18:13:44Z | |
dc.date.available | 2017-04-12T18:13:44Z | |
dc.date.issued | 2009-10-16 | |
dc.identifier.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 | en_US |
dc.identifier.uri | http://hdl.handle.net/1808/23641 | |
dc.description.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. | en_US |
dc.publisher | American Chemical Society | en_US |
dc.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. | en_US |
dc.subject | Schmidt reaction | en_US |
dc.subject | Lactam synthesis | en_US |
dc.subject | Azides | en_US |
dc.subject | Domino reaction | en_US |
dc.subject | Sakurai reaction | en_US |
dc.subject | Stereoselective aldol reaction | en_US |
dc.subject | Titanium enolate | en_US |
dc.subject | GOESY | en_US |
dc.title | One-pot Synthesis of Lactams Using Domino Reactions: Combination of Schmidt Reaction with Sakuri and Aldol Reaction | en_US |
dc.type | Article | en_US |
kusw.kuauthor | Huh, Chan Woo | |
kusw.kuauthor | Somal, Gagandeep K. | |
kusw.kuauthor | Katz, Christopher E. | |
kusw.kuauthor | Pei, Huanxing | |
kusw.kuauthor | Zeng, Yibin | |
kusw.kuauthor | Douglas, Justin T. | |
kusw.kuauthor | Aubé, Jeffrey | |
kusw.kudepartment | Medicinal Chemistry | en_US |
dc.identifier.doi | 10.1021/jo901843w | en_US |
dc.identifier.orcid | https://orcid.org/0000-0003-1049-5767 | |
kusw.oaversion | Scholarly/refereed, author accepted manuscript | en_US |
kusw.oapolicy | This item meets KU Open Access policy criteria. | en_US |
dc.rights.accessrights | openAccess | |