389090-87-3Relevant academic research and scientific papers
A Phosphine-Catalyzed Novel Asymmetric [3+2] Cycloaddition of C,N-Cyclic Azomethine Imines with δ-Substituted Allenoates
Wang, De,Lei, Yu,Wei, Yin,Shi, Min
, p. 15325 - 15329 (2014)
Catalytic asymmetric [3+2] cycloadditions of C,N-cyclic azomethine imines with δ-substituted allenoates have been developed in the presence of (S)-Me-f-KetalPhos, affording functionalized tetrahydroquinoline frameworks in good yields with high diastereo- and good enantioselectivities under mild condition. The substrate scope has been also examined. This is the first time that δ-substituted allenoates have been applied as a δ,γ-C-C bond participated C 2 synthon in asymmetric synthesis. Another round: Catalytic asymmetric [3+2] cycloaddition of C,N-cyclic azomethine imines with δ-substituted allenoates have been developed in the presence of (S)-Me-f-KetalPhos, affording functionalized tetrahydroquinoline frameworks in good yields with high diastereo- and good enantioselectivities under mild conditions. This is the first example applying δ-substituted allenoates as C 2 synthons in asymmetric δ,γ-C-C bond formation.
CuBr2 catalyzed bromination/oxidation of isochromans to benzaldehyde derivatives
Zhou, Mei-Yan,Kong, Shan-Shan,Zhang, Ling-Qiong,Zhao, Ming,Duan, Jin-Ao,Ou-Yang, Zhen,Wang, Min
supporting information, p. 3962 - 3964 (2013/07/25)
A series of isochromans were oxidized and brominated by using 1.2 equiv of CuBr2 in CH3CN at reflux to give the corresponding bromo benzaldehydes in moderate yields. A plausible mechanism for this transformation has been suggested.
Copper-catalyzed enantioselective additions to oxocarbenium ions: Alkynylation of isochroman acetals
Maity, Prantik,Srinivas, Harathi D.,Watson, Mary P.
, p. 17142 - 17145 (2011/12/13)
We have developed an enantioselective, copper(I)-catalyzed addition of terminal alkynes to racemic isochroman acetals. This method is one of the first transition-metal-catalyzed approaches to enantioselective additions to prochiral oxocarbenium ions. In this reaction, TMSOTf is used to form the oxocarbenium ion in situ under conditions compatible with simultaneous formation of the chiral copper acetylide. By using a bis(oxazoline) ligand, good yields and enantioselectivities are observed for a variety of enantioenriched 1-alkynyl isochromans.
Catalytic enantioselective 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines with α,β-unsaturated aldehydes
Hashimoto, Takuya,Maeda, Yuko,Omote, Masato,Nakatsu, Hiroki,Maruoka, Keiji
supporting information; experimental part, p. 4076 - 4077 (2010/05/15)
(Figure Presented) A yet-unexploited class of azomethine imines, C,N-cyclic azomethine imines, could be successfully employed in highly enantioselective 1,3-dipolar cycloaddition with enals catalyzed by titanium-BINOLate to give pharmaceutically attractive tetrahydroisoquinoline and piperidine motifs. Copyright
