1169855-54-2Relevant academic research and scientific papers
Asymmetric synthesis of tetrahydropyran[3,2-c]quinolinones via an organocatalyzed formal [3 + 3] annulation of quinolinones and MBH 2-naphthoates of nitroolefin
Li, Jian,Hu, Qi-Long,Chen, Xue-Ping,Hou, Ke-Qiang,Chan, Albert S.C.,Xiong, Xiao-Feng
, p. 697 - 700 (2019/09/30)
An efficient asymmetric and enantio-swithchable organocatalytic [3 + 3] annulation reaction using MBH-2-naphthoates of nitroalkenes and 4-hydroxyquinolin-2(1H)-ones has been developed. Densely substituted tetrahydropyrano[3,2-c]quinolinones scaffolds with two adjacent stereogenic centers are obtained with high yield (up to 95% yield) and good stereoselectivities (up to >20:1 dr and 96% ee) in an enantio-switchable manner. Furthermore, gram scale synthesis was achieved and the nitro group could easily transform into an amino group without any appreciable loss in the diastereo- and enantioselectivity.
Stereoselective Synthesis of 3-Oxabicyclo[3.3.1]Nonan-2-Ones via a Domino Reaction Catalyzed by Modularly Designed Organocatalysts
Parella, Ramarao,Jakkampudi, Satish,Arman, Hadi,Zhao, John C.-G.
supporting information, p. 208 - 213 (2018/12/04)
A highly stereoselective method for the synthesis of functionalized 3-oxabicyclo[3.3.1]nonan-2-one derivatives with four contiguous stereogenic centers, including one tetrasubstituted stereogenic center, was realized through an organocatalytic domino Mich
Enantioselective construction of oxa- and aza-angular triquinanes through tandem [4 + 1]/[3 + 2] cycloaddition of sulfur ylides and nitroolefins
An, Jing,Lu, Liang-Qiu,Yang, Qing-Qing,Wang, Tao,Xiao, Wen-Jing
supporting information, p. 542 - 545 (2013/04/10)
A formal [4 + 1]/[3 + 2] cycloaddition sequence of sulfur ylides and alkene-tethered nitroolefins has been developed. The use of (R)-binol-derived chiral sulfide leads to an asymmetric process that allows the construction of oxa- and aza-angular triquinanes in good to excellent diastereo- and enantioselectivities.
Cooperative dienamine/hydrogen-bonding catalysis: Enantioselective formal [2+2] cycloaddition of enals with nitroalkenes
Talavera, Garazi,Reyes, Efraím,Vicario, Jose L.,Carrillo, Luisa
supporting information; experimental part, p. 4104 - 4107 (2012/06/04)
Two can play this game: The title reaction is catalyzed by a chiral secondary amine in the presence of an achiral thiourea for the enantio- and diastereoselective synthesis of highly functionalized cyclobutanes (see scheme; TMS=trimethylsilyl). Mechanistically, two consecutive Michael reactions proceed through an unprecedented combination of an dienamine/iminium activation mode. Copyright
1,3-dipolar cycloaddition on baylis-hillman adducts: Novel synthesis of pyrrolidines, spiropyrrolidines, and spiropyrrolizidines
Bakthadoss, Manickam,Sivakumar, Nagappan,Devaraj, Anthonisamy,Sharada, Duddu S.
experimental part, p. 2136 - 2146 (2011/08/05)
A facile regio- and stereoselective synthesis of functionalized pyrrolidines, spiropyrrolidines, and spiropyrrolizidines using the Baylis-Hillman adducts derived from nitroolefins via intermolecular [3+2]-cycloaddition reaction is reported. Georg Thieme Verlag Stuttgart ? New York.
