title: Phosphine-catalyzed [3 + 2] cycloaddition of sulfamate-derived cyclic imines with allenoate: synthesis of sulfamate-fused dihydropyrroles.
abstract: Ph3P-catalyzed [3 + 2] cycloaddition reaction of sulfamate-derived cyclic imines with allenoate has been developed, affording sulfamate-fused dihydropyrroles under very mild conditions in high yields. Using amino acid-based bifunctional phosphine as chiral catalyst, its asymmetric variant provided the corresponding products in good yields with moderate to excellent enantiomeric excesses (up to 91% yield and up to 98% ee). Subsequent transformations of the heterocyclic products gave various pharmaceutically attractive compounds.
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, PR China.
authors.forename: Hao
authors.initials: H
authors.lastname: Yu
authors.forename: Lei
authors.initials: L
authors.lastname: Zhang
authors.forename: Zhilin
authors.initials: Z
authors.lastname: Yang
authors.forename: Zhen
authors.initials: Z
authors.lastname: Li
authors.forename: Yan
authors.initials: Y
authors.lastname: Zhao
authors.forename: Yumei
authors.initials: Y
authors.lastname: Xiao
authors.forename: Hongchao
authors.initials: H
authors.lastname: Guo
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D002087:Butyrates / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013451:Sulfonic Acids / Q000737:chemistry*
chemical_list: D000466:Alkadienes; D002087:Butyrates; D007097:Imines; D010720:Phosphines; D011758:Pyrroles; D013451:Sulfonic Acids; C005741:sulfamic acid; C044646:phosphine