94664-79-6Relevant articles and documents
Synthesis of Benzimidazolones via One-Pot Reaction of Hydroxylamines, Aldehydes, and Trimethylsilyl Cyanide Promoted by Diacetoxyiodobenzene
Zhang, Huaiyuan,Huang, Danfeng,Wang, Ke-Hu,Li, Jun,Su, Yingpeng,Hu, Yulai
, p. 1600 - 1609 (2017/02/10)
A novel and efficient PhI(OAc)2-promoted one-pot reaction of aromatic hydroxylamines, aldehydes, and TMSCN in the presence of BF3·Et2O is described. A wide variety of N-substituted benzimidazolones are obtained with satisfactory yields under mild reaction conditions. The method was proven to be efficient for the synthesis of benzimidazolone derivatives from readily available starting materials.
A highly stereoselective synthesis of chiral α-amino-β-lactams via the Kinugasa reaction employing ynamides
Zhang, Xuejun,Hsung, Richard P.,Li, Hongyan,Zhang, Yu,Johnson, Whitney L.,Figueroa, Ruth
supporting information; experimental part, p. 3477 - 3479 (2009/05/27)
(Chemical Equation Presented) A highly stereoselective synthesis of chiral α-amino-β-lactam through an ynamide-Kinugasa reaction is described. In addition, a mechanistic model is illustrated here to rationalize the observed diastereoselectivity, which depends on both the initial [3 + 2] cycloaddition step and the subsequent protonation for which both are highly selective.
Cu(I)/Bis(azaferrocene)-catalyzed enantioselective synthesis of β-lactams via couplings of alkynes with nitrones
Lo, Michael M.-C.,Fu, Gregory C.
, p. 4572 - 4573 (2007/10/03)
As a consequence of the wide-ranging significance of β-lactams (e.g., use as drugs and as chiral building blocks), a great deal of effort has been dedicated to the development of methods for their stereoselective synthesis. Although considerable progress has been achieved, nearly all of the approaches that have been described are based on the use of chiral precursors; direct catalytic enantioselective routes to β-lactams are rare as well as limited in scope. In this communication, we establish that, using a new C2-symmetric planar-chiral bis(azaferrocene) ligand, we can generate β-lactams with very good enantiomeric excess and cis diastereoselection via catalytic enantioselective Kinugasa reactions (couplings of alkynes with nitrones). Appealing attributes of this process include the ready availability of the starting materials, the functional-group tolerance of the reaction, and the convergency of the approach. Copyright
