Efficient synthesis of methylenetetrahydrofurans and methylenepyrrolidines by formal [3+2] cycloadditions of propargyl substrates.
Recent developments concerning the synthesis of methylenetetrahydrofurans and methylenepyrrolidines by one-pot formal [3+2] cycloadditions involving propargylic (and allylic) alcohols and amines with electrophilic alkenes are described. The synthetic methods provide powerful tools to prepare highly functionalized oxygen- and nitrogen-containing five-membered ring systems. The reactions can be effectively promoted by base, base/transition metals, and Lewis acids, depending on the substrates.
Yamazaki
Shoko
S
Department of Chemistry, Nara University of Education, Takabatake-cho, Nara 630-8528, Japan. yamazaks@nara-edu.ac.jp
D000438:Alcohols / Q000737:chemistry; D000473:Alkanes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D003300:Copper / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D008314:Malonates / Q000737:chemistry; D008745:Methylation; D015394:Molecular Structure; D017672:Nitrogen Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D010293:Pargyline / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D015032:Zinc / Q000737:chemistry
D000438:Alcohols; D000473:Alkanes; D000480:Alkynes; D005663:Furans; D008314:Malonates; D017672:Nitrogen Compounds; D011759:Pyrrolidines; D010165:Palladium; D003300:Copper; D010293:Pargyline; D015032:Zinc