2327-22-2Relevant academic research and scientific papers
Chiral Phosphoric Acid-Catalyzed Enantioselective Synthesis of Pyrazole-Based Unnatural α-Amino Acid Derivatives
Woldegiorgis, Alemayehu Gashaw,Han, Zhao,Lin, Xufeng
supporting information, p. 274 - 280 (2021/11/01)
An enantioselective synthesis of unnatural pyrazole-based α-chiral amino acid derivatives from the asymmetric reaction of N-aryl-5-aminopyrazoles with β,γ-alkynyl-α-imino esters using a chiral spirocyclic phosphoric acid catalyst was developed. Using the established methodology, various pyrazole-based α-amino acid derivatives with tetrasubstituted carbon stereocenters were obtained in 67–98% yields and with 73–99% enantioselectivities. The NH2 functionality in the corresponding products enables further transformations to a chiral thiourea and a lactam. (Figure presented.).
Organocatalytic Asymmetric Dearomatization Reaction for the Synthesis of Axial Chiral Allene-Derived Naphthalenones Bearing Quaternary Stereocenters
Woldegiorgis, Alemayehu Gashaw,Han, Zhao,Lin, Xufeng
, p. 6606 - 6611 (2021/09/02)
The highly regio-, diastereo-, and enantioselective dearomatization reaction of 1-substituted 2-naphthols and β,γ-alkynyl-α-imino esters with complete atom economy is disclosed via chiral phosphoric acid catalysis. This protocol provides facile and effici
Organocatalytic Enantioselective Synthesis of Tetrasubstituted α-Amino Allenoates by Dearomative γ-Addition of 2,3-Disubstituted Indoles to β,γ-Alkynyl-α-imino Esters
Yang, Junxian,Wang, Zheng,He, Zeyuan,Li, Guofeng,Hong, Liang,Sun, Wangsheng,Wang, Rui
supporting information, p. 642 - 647 (2019/11/28)
The first asymmetric synthesis of tetrasubstituted α-amino allenoates by a chiral phosphoric acid catalyzed dearomative γ-addition reaction of 2,3-disubstituted indoles to β,γ-alkynyl-α-imino esters is reported. This method provides access to a series of
Chiral Phosphine-Silver(I) Complex Catalyzed Enantioselective Interrupted Feist-Bénary Reaction with Ynones: The Aldol-Cycloisomerization Cascade
Sinha, Debarshi,Biswas, Arnab,Singh, Vinod K.
supporting information, p. 3302 - 3305 (2015/07/15)
(Chemical Equation Presented) Silver-catalyzed interrupted Feist-Bénary reaction is described for the efficient enantioselective synthesis of dihydrofuran heterocycles. A new method has been developed for the silver(I)-(R)-BINAP complex mediated aldol-cyc
Catalytic Enantioselective Quick Route to Aldol-Tethered 1,6- and 1,7-Enynes from ω-Unsaturated Aldehydes
García, Jesús M.,Odriozola, José M.,Razkin, Jesús,Lapuerta, Irati,Odriozola, Amaiur,Urruzuno, I?aki,Vera, Silvia,Oiarbide, Mikel,Palomo, Claudio
supporting information, p. 15543 - 15554 (2016/02/18)
An effective asymmetric route to functionalized 1,6- and 1,7-enynes has been developed based on a direct cross-aldol reaction between ω-unsaturated aldehydes and propargylic aldehydes (α,β-ynals) promoted by combined α,α-dialkylprolinol ether/Br?nsted acid catalysis. This synergistic activation strategy is key to accessing the corresponding aldol adducts with high stereoselectivity, both enantio- and diastereoselectivity. The aldol reaction also proceeds well with propargylic ketones (α,β-ynones) thus enabling a stereocontrolled access to the corresponding tertiary alcohols. The utility of these adducts, which are difficult to prepare through standard methodology, is demonstrated by their transformation into trisubstituted bicyclic enones using standard Pauson-Khand conditions.
Three-component assembly and divergent ring-expansion cascades of functionalized 2-iminooxetanes
Yao, Weijun,Pan, Lianjie,Zhang, Yiping,Wang, Gang,Wang, Xiaoqin,Ma, Cheng
supporting information; experimental part, p. 9210 - 9214 (2011/02/23)
A bold diversification strategy: Aromatic alkynes, p-toluenesulfonyl azide, and aromatic 2-oxobut-3-ynoates underwent a copper(I)-catalyzed multicomponent reaction to provide functionalized 2-iminooxetanes 1, which could be converted selectively into five-membered nitrogen-containing heterocycles of two different sorts, depending on the reaction conditions (see scheme; Tf= trifluoromethanesulfonyl; R=Et, iPr). Copyright
