58775-64-7Relevant academic research and scientific papers
Synthesis of Spirolactams and Fused Bicyclic Lactams via Acid-Promoted Cyclolactamization of (Ethynyl(tosyl)amino)methyl-Tethered Cyclohex-2-enols
Tung, Po-Ting,Zhong, Chang-Zhi,Chien, Tzu-Chiang,Yeh, Ming-Chang P.
, p. 11543 - 11557 (2017/11/10)
A simple synthetic method to construct the spirolactam framework from TfOH-catalyzed spirolactamization of cyclohex-2-enols bearing a tethered (arylethynyl(tosyl)amino)methyl moiety is described. The reaction proceeded through a keteniminium-allylic carbocation intermediate. Hydration of the keteniminium ion, followed by attack of the resulting enolate onto the tethered allylic carbocation, provided the spirolactam ring skeleton. This strategy could also be employed in the synthesis of fused bicyclic lactams from BF3·OEt2-assisted cyclolactamization of TBS-protected 2-(ethynyl(tosyl)amino)methylcyclohex-2-enols.
Synthesis of 2-azaspiro[4.6]undec-7-enes from N -tosyl- N -(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols
Yeh, Ming-Chang P.,Liang, Chia-Jung,Fan, Chern-Wei,Chiu, Wei-Hang,Lo, Jun-Yuan
, p. 9707 - 9717,11 (2012/12/12)
The FeCl3-promoted synthesis of 2-azaspiro[4.6]undec-7-ene rings proceeds via ring expansion/cyclization/chlorination of N-tosyl-N-(3- arylpropargyl)-tethered 6-methylbicyclo[4.1.0]heptan-2-ols. This azaspirocyclic ring skeleton can also be obtained in one pot from the tert-butyldimethylsilyl- protected N-tosyl-N-(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols and diethylzinc/diiodomethane.
Facile synthesis of azaspirocycles via iron trichloride-promoted cyclization/chlorination of cyclic 8-Aryl-5-aza-5-tosyl-2-en-7-yn-1-ols
Yeh, Ming-Chang P.,Fang, Cheng-Wei,Lin, Hsin-Hui
body text, p. 1830 - 1833 (2012/07/03)
A simple and efficient FeCl3-promoted cyclization/chlorination of cyclic tosylamine-tethered 8-aryl-2-en-7-yn-1-ols was observed. The reaction proceeded instantaneously at 23 °C in air to afford (Z)-4- (arylchloromethylene)-substituted azaspiro
Trifluoromethanesulfonic acid-catalyzed tandem semi-pinacol rearrangement/alkyne-aldehyde metathesis reaction of arylpropagylsulfonamide- tethered 2,3-epoxycyclohexan-1-ols to spiropiperidines
Lin, Ming-Nan,Wu, Shih-Hui,Yeh, Ming-Chang P.
body text, p. 3290 - 3294 (2012/01/16)
A simple and efficient trifluoromethanesulfonic acid-catalyzed cycloisomerization of arylpropagylsulfonamide-tethered 2,3-epoxycyclohexan-1-ols is described. The cyclization proceeds via tandem semi-pinacol rearrangement/alkyne-aldehyde metathesis to affo
Palladium-Catalyzed Preparation of Carbon and Oxygen Spirocycles
Godleski, Stephen A.,Valpey, Richard S.
, p. 381 - 383 (2007/10/02)
A variety of substituted spiroundecene and spirodecene systems have been prepared by utilizing ?-allylpalladium chemistry in the key ring-forming step.
