Indium-mediated selective introduction of a 1,3-butadien-2-yl group at the C4-position in 2-azetidinones and application of 1,3-diene-tethered 2-azetidinones in the Diels-Alder reaction.
The reaction of 4-acetoxy-2-azetidinones with organoindium reagents generated in situ from indium and 1,4-dibromo-2-butyne in the presence of LiCl in DMF selectively produced 2-azetidinones which contain a 1,3-butadienyl-2-yl group at the C4-position in good yields. The Diels-Alder reaction of 4-[(1-methylene)prop-2-enyl]-2-azetidinones with a variety of dienophiles provided 2-azetidinones with valuable functional-group-substituted six-membered rings at the C4-position in good yields.
Lee
Kooyeon
K
National Research Laboratory of Catalytic Organic Reaction, Department of Chemistry and Institute for Basic Science, Kangwon National University, Chunchon 200-701, Republic of Korea.
Lee
Phil Ho
PH
D000480:Alkynes / Q000737:chemistry; D001384:Azetidines / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D007204:Indium / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*
C116379:2-azetidinone; D000480:Alkynes; D001384:Azetidines; D009942:Organometallic Compounds; D007204:Indium