Modular evolution of a chiral auxiliary for the 1,3-dipolar cycloaddition of isomünchnones with vinyl ethers.
[reaction: see text]. The 1,3-dipolar cycloaddition reaction has long been recognized as a powerful methodology in organic synthesis. More recently, this reaction has become a popular manifold for the construction of chemical diversity. Herein, we report the development of a chiral template for the facially selective cycloaddition of isomünchnones, a common class of 1,3-dipoles. The modular format of the asymmetric unit allowed a systematic optimization of selectivity. In addition, the chiral auxiliary was removed through an unusually facile ester aminolysis.
Savinov
Sergey N
SN
Department of Chemistry, Yale University, New Haven, Connecticut 06511, USA.
Austin
David J
DJ
D000596:Amino Acids / Q000737:chemistry; D001391:Azo Compounds / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D018360:Crystallography, X-Ray; D003500:Cyclization; D006860:Hydrogen Bonding; D007202:Indicators and Reagents; D007783:Lactones / Q000737:chemistry*; D008958:Models, Molecular; D014753:Vinyl Compounds / Q000737:chemistry*
D000596:Amino Acids; D001391:Azo Compounds; D007202:Indicators and Reagents; D007783:Lactones; D014753:Vinyl Compounds; C100195:vinyl ether