Gold catalyzed cycloisomerization of propargylic alcohols and acetates as synthetic strategies to N-heterocycles

• Main Author: Dewi Susanti
• Other Authors: Wai Hong Chan, Philip
• Format: Theses and Dissertations
• Language: English
• Published: 2014
• Subjects: DRNTU::Science::Biological sciences::Biochemistry
• Online Access: https://hdl.handle.net/10356/61849
• Institution: Nanyang Technological University

This thesis will focus on the development of new methodologies utilizing propargylic alcohols and acetates in gold catalyzed strategies to potentially synthetically useful N-heterocycles. The protocols developed include tandem 1,3-migration/[2+2] cycloaddition of enantiopure 1,7-enyne benzoates in the presence of a gold(I) complex to form stereochemically well-defined azabicyclo[4.2.0]oct-5-enes and gold(I) catalyzed cycloisomerization and Diels-Alder reaction of 1,4,9-dienyne esters to 3a,6-methanoisoindole esters. In the course of our study on gold catalyzed reactions of propargylic alcohols, it was found that silver salts could also serve as a possible alternative to the third row metal as the catalyst to mediate the construction of indolin-3-ol derivatives via intramolecular hydroamination of 2-aminophenylprop-1-yn-3-ols. From this investigation, during examining the scope of the hydroamination reaction to include alkyl protected 2-aminophenylprop-1-yn-3-ols, an unexpected reaction leading to the formation of 2-oxindoles in the presence of silica gel is also presented.