A regio- and stereoselective approach to quaternary centers from chiral trisubstituted aziridines

被引：0
|
作者：
Forbeck, Erin M. [1 ]
Evans, Cory D. [1 ,2 ]
Gilleran, John A. [1 ]
Li, Pixu [1 ,3 ]
Joullié, Madeleine M. [1 ]
机构：
[1] Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA 19104, United States
[2] Food and Drug Administration-CVM, MPN2 RME 324 HFV-142, 7500 Standish Place, Rockville, MD 20855, United States
[3] Wyeth Research, 401 N. Middletown Rd., Pearl River, NY 10965, United States
来源：
Journal of the American Chemical Society | 2007年 / 129卷 / 46期
关键词：
A thorough investigation of a regio- and stereospecific aziridine ring opening reaction presents new synthetic technology for the construction of a variety of quaternary β-substituted-α-amino functional groups. Mild; metal-free reaction conditions allow for application in highly functionalized systems. This reaction has been applied to the challenging stereoselective formation of tertiary alkyl-aryl ethers. The strategy for the formation of these hindered ethers has been investigated using a variety of functionalized aziridines and phenols to determine the scope of the reaction. Other nucleophiles; such as thiolate; azide; and chloride; have also been examined to encompass the synthesis of a broader range of functionalities. This aziridine ring opening reaction manifold has demonstrated utility in assembling: β-substituted-α-amino carboxamides; β-substituted-α-amino esters; β-substituted-α-amino silyl ethers; β-thio-α-amino carboxamides; β-azido-α-amino carboxamides; and β-halo-α- amino carboxamides. Studies to probe the effect of the aziridine substitution patterns show that alkyl aziridines display similar reactivity to alkynyl aziridines; giving insight into mechanistic possibilities. © 2007 American Chemical Society;
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摘要：
Journal article (JA)
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页码：14463 / 14469
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