876337-33-6Relevant academic research and scientific papers
Enantioselective Black rearrangement catalyzed by chiral bicyclic imidazole
Wang, Mingli,Zhang, Zhenfeng,Liu, Shan,Xie, Fang,Zhang, Wanbin
supporting information, p. 1227 - 1230 (2014/02/14)
A newly developed chiral imidazole nucleophilic catalyst, Acyloxy-DPI, was readily prepared and successfully applied to the enantioselective Black rearrangement with up to 88% ee for a wide range of substrates possessing different substituted groups. A pl
N-heterocyclic carbene catalysed oxygen-to-carbon carboxyl transfer of indolyl and benzofuranyl carbonates
Thomson, Jennifer E.,Kyle, Andrew F.,Gallagher, Katherine A.,Lenden, Philip,Concellon, Carmen,Morrill, Louis C.,Miller, Andrew J.,Joannesse, Caroline,Slawin, Alexandra M. Z.,Smith, Andrew D.
experimental part, p. 2805 - 2818 (2009/04/04)
The ability of N-heterocyclic carbenes to promote O-to-C carboxyl transfer on a range of indolyl and benzofuranyl carbonates is examined, and the scope and limitations of this process delineated. Georg Thieme Verlag Stuttgart.
Enantioselective TADMAP-catalyzed carboxyl migration reactions for the synthesis of stereogenic quaternary carbon
Shaw, Scott A.,Aleman, Pedro,Christy, Justin,Kampf, Jeff W.,Va, Porino,Vedejs, Edwin
, p. 925 - 934 (2007/10/03)
The chiral, nucleophilic catalyst TADMAP [1, 3-(2,2,2-triphenyl-1- acetoxyethyl)-4-(dimethylamino)-pyridine] has been prepared from 3-lithio-4-(dimethylamino)pyridine (5) and triphenylacetaldehyde (3), followed by acylation and resolution. TADMAP catalyzes the carboxyl migration of oxazolyl, furanyl, and benzofuranyl enol carbonates with good to excellent levels of enantioselection. The oxazole reactions are especially efficient and are used to prepare chiral lactams (23) and lactones (30) containing a quaternary asymmetric carbon. TADMAP-catalyzed carboxyl migrations in the indole series are relatively slow and proceed with inconsistent enantioselectivity. Modeling studies (B3LYP/6-31G*) have been used in qualitative correlations of catalyst conformation, reactivity, and enantioselectivity.
