Cycloisomerization of 1,n-enyne and 1,n-diyne esters and carbonates to cyclic compounds via gold catalysis

• Main Author: Sally
• Other Authors: Chan Wai Hong, Philip
• Format: Theses and Dissertations
• Language: English
• Published: 2015
• Subjects: DRNTU::Science::Chemistry::Biochemistry
• Online Access: https://hdl.handle.net/10356/65470
• Institution: Nanyang Technological University

Organic compounds containing the azahetero-, carbo- and spirocylic structural motif are commonly found in a myriad of natural products and synthetic molecules of potent biological activity and materials applications. Gold catalyzed cycloisomerization of 1,n-enyne and 1,n-diyne systems have emerged as one of the most widely explored strategies to construct these cyclic compounds, particularly in intramolecular cycloisomerization reactions due to its atom economical nature. In such, we explored three methodologies of accessing cyclic compounds utilizing this approach. First, we developed an efficient gold(I) catalyzed cycloisomerization of 1,7-enyne esters as a viable method for the synthesis of various cis-1,2,3,6-tetrahydropyridin-4-yl ketones and -diketones. Next, we delienated the cycloisomerization of 1,6,8-dienyne carbonates and esters to the formation of cis-cyclohepta-4,8-diene-fused pyrrolidines. Lastly, a tandem [2,3]-sigmatropic rearrangement/Nazarov cyclisation/6-exo-dig cyclisation/1,5-acyl migration of 1-ene-4,10-diyne esters was explored.