66696-84-2Relevant articles and documents
A donor-acceptor cyclopropene as a dipole source for a silver(i) catalyzed asymmetric catalytic [3+3]-cycloaddition with nitrones
Xu, Xinfang,Zavalij, Peter J.,Doyle, Michael P.
, p. 10287 - 10289 (2013)
Silver(i)-catalyzed asymmetric formal [3+3]-cycloaddition of nitrones with a donor-acceptor cyclopropene, formed in situ from dirhodium acetate-catalyzed dinitrogen extrusion/intramolecular cyclization of enoldiazoacetates, effectively generates 3,6-dihydro-1,2-oxazine derivatives in high yield and with exceptional stereocontrol.
5-Carbonyl-1,3-oxazine-2,4-diones from N-Cyanosulfoximines and Meldrum's Acid Derivatives
Brosge, Felix,Kochs, Johannes Florian,Bregu, Mariela,Truong, Khai-Nghi,Rissanen, Kari,Bolm, Carsten
supporting information, p. 6667 - 6670 (2020/09/02)
At elevated temperatures, N-cyanosulfoximines react with Meldrum's acid derivatives to give sulfoximines with N-bound 5-carbonyl-1,3-oxazine-2,4-dione groups. A representative product was characterized by single-crystal X-ray structure analysis. The product formation involves an unexpected molecular reorientation requiring several sequential bond-forming and-cleaving processes.
Enantioselective Carbene Cascade: An Effective Approach to Cyclopentadienes and Applications in Diels–Alder Reactions
Wang, Xiangbo,Zhou, Yunfei,Qiu, Lihua,Yao, Ruwei,Zheng, Yang,Zhang, Cheng,Bao, Xiaoguang,Xu, Xinfang
supporting information, p. 1571 - 1576 (2016/10/13)
An asymmetric carbene cascade reaction, which proceeds through carbene/alkyne metathesis and formal (3+2) cycloaddition and converts alkynyl-tethered enol diazoacetates to chiral bicyclic cyclopentadienes, is presented; and no catalytic asymmetric version of these carbene cascade transformations has been disclosed so far. The proton signals of the cyclopropene intermediates are observed in the mechanism study, which clearly demonstrate the reaction pathways. In addition, these products are intercepted via Diels–Alder reactions to provide bridged polycyclic structures in high yields and enantioselectivities. (Figure presented.).
Practical, asymmetric route to sitagliptin and derivatives: Development and origin of diastereoselectivity
Gutierrez, Osvaldo,Metil, Dattatray,Dwivedi, Namrata,Gudimalla, Nagaraju,Chandrashekar,Dahanukar, Vilas H.,Bhattacharya, Apurba,Bandichhor, Rakeshwar,Kozlowski, Marisa C.
supporting information, p. 1742 - 1745 (2015/04/14)
The development of a practical and scalable process for the asymmetric synthesis of sitagliptin is reported. Density functional theory calculations reveal that two noncovalent interactions are responsible for the high diastereoselection. The first is an intramolecular hydrogen bond between the enamide NH and the boryl mesylate S=O, consistent with MsOH being crucial for high selectivity. The second is a novel C-H···F interaction between the aryl C5-fluoride and the methyl of the mesylate ligand.