215509-18-5Relevant articles and documents
Enantioselective Synthesis of 1-Substituted 1,2,3,4-Tetrahydroisoquinolines through 1,3-Dipolar Cycloaddition by a Chiral Phosphoric Acid
Akiyama, Takahiko,Honma, Yasuhiro,Jin, Yuan,Miyagawa, Masamichi,Morita, Hisashi
supporting information, p. 1541 - 1545 (2019/08/07)
A new approach is described for the asymmetric synthesis of 1-substituted 1,2,3,4-tetrahydroisoquinolines that is based on the enantioselective 1,3-dipolar cycloaddition reaction of a nitrone and a vinyl ether in the presence of a chiral phosphoric acid that gives the chiral tetrahydroisoquinolines in high yields and with high enantioselectivities. 1 H and 31 P NMR analyses of the mixture of nitrone and chiral phosphoric acid suggest the formation of a 1:1 complex.
Catalytic enantioselective 1,3-dipolar cycloaddition reactions of cyclic nitrones: A simple approach for the formation of optically active isoquinoline derivatives
Jensen,Roberson,Jorgensen
, p. 9080 - 9084 (2007/10/03)
The first highly diastereo- and enantioselective catalytic 1,3-dipolar cycloaddition reaction of cyclic nitrones activated by chiral Lewis acids with electron-rich alkenes has been developed. The nitrones, mainly 3,4-dihydroisoquinoline N-oxides, are activated by chiral 3,3′-aryl BINOL-AlMe complexes and undergo a regio-, diastereo-, and enantioselective 1,3-dipolar cycloaddition reaction with especially alkyl vinyl ethers, giving the exo diastereomer of the cycloaddition products in high yield, >90% de and up to 85% ee. The reaction has been investigated under various conditions, and it is demonstrated that the reaction is an attractive synthetic procedure for the introduction of a chiral center in the 1-position of the isoquinoline skeleton. The mechanism of the reaction is discussed on the basis of the assignment of the absolute configuration of the cycloaddition product and theoretical calculations.
Palladium(II)-catalyzed 1,3-dipolar cycloaddition of nitrones with enol ethers
Hori, Kazushige,Ito, Junji,Ohta, Tetsuo,Furukawa, Isao
, p. 12737 - 12744 (2007/10/03)
The 1,3-dipolar cycloadditions of enol ethers as electron-rich olefins with C-phenyl-N-alkyl nitrones proceeded smoothly in the presence of easy handling palladium(II) catalysts under mild conditions to give isoxazolidines in good yield.
1,3-Dipolar cycloaddition reactions of nitrones with alkyl vinyl ethers catalyzed by chiral oxazaborolidines
Seerden, Jean-Paul G.,Boeren, Mike M. M.,Scheeren, Hans W.
, p. 11843 - 11852 (2007/10/03)
The 1,3-dipolar cycloaddition reactions of various Z- and E-nitrones with ethyl vinyl ether and 2,3-dihydrofuran are catalyzed by 20 mol% of chiral oxazaborolidines at room temperature. The effect of high pressure on these reactions is discussed.
