(一) Lewis Acid-Promoted Intramolecular Cyclization of Silyl- Protected 2-(3-Arylpropargyltosylamino)methylcyclohex- 2-en-1-ols : Synthesis of Isoquinoline Derivatives (二) Brønsted Acid-Assisted Alkyne-Aldehyde Metathesis of 1-(3-Arylprop-2-yn-1-yl)-2-formylpyrrolidine : Synthesis of Pyrrolizine Derivatives

• Main Author: 黃鈺雅
• Other Authors: 葉名倉
• Format: Others
• Language: zh-TW
• Published: 2014
• Online Access: http://ndltd.ncl.edu.tw/handle/09935030685465322120

碩士 === 國立臺灣師範大學 === 化學系 === 102 === This thesis focuses on acid-promoted intramolecular cyclization of N-containing O-silyl-protected enynols and N-containing ynals. Three major reactions are discussed. First, FeCl3-promoted cyclization of O-silyl-protected 2-(3-arylpropargyltosylamino)methylcyclohex-2-en-1-ols in the air at room temperature produced isoquinoline derivatives containing an aryl(chloro)methylene moiety. In this process, FeCl3 acts as both the activating group and the chloride source. Second, BF3-promoted intramolecular cyclization of O-silyl-protected 2-(3-arylpropargyltosylamino)methylcyclohex- 2-en-1-ols in CH3CN at room temperature in the air provided octahydroisoquinolines having an amide moiety. Third, NHTf2-assisted alkyne-aldehyde metathesis of 1-(3-phenylprop-2-yn-1-yl)-2-formyl- pyrrolidine afforded tetrahydropyrrolizines at 80 ℃ under an atmosphere of nitrogen. The 2,3,5,7a-tetrahydro-1H-pyrrolizines gradually aromatized to 2,3-dihydro-1H-pyrrolizines in the air at ambient temperature.