title: Enantioselective Construction of Spiro[indoline-3,2'-pyrrole] Framework via Catalytic Asymmetric 1,3-Dipolar Cycloadditions Using Allenes as Equivalents of Alkynes.
abstract: The first catalytic asymmetric 1,3-dipolar cycloadditions (1,3-DCs) of isatin-derived azomethine ylide with allenes have been established, which efficiently assembly isatins, amino-esters and 2,3-allenoate into enantioenriched spiro[indoline-3,2'-pyrrole] derivatives with a quaternary stereogenic center in generally high enantioselectivities (80-98% ee). In this allene-involved 1,3-DC, an unexpected spirooxindole framework bearing an intra-annular C═C double bond was generated, which is quite different from previously reported 1,3-DCs of allenes. This approach not only confronted the great challenge in using allenes as dipolarophiles of 1,3-DCs, but also provided a unique strategy of using allenes as equivalents of alkynes to construct spiro[indoline-3,2'-pyrrole] structure. Besides, this reaction also represents the first catalytic asymmetric ketone-involved 1,3-DCs of allenes, which will also greatly enrich the research contents of 1,3-DCs, the chemistry of allenes as well as the synthetic methods of spirooxindoles.
authors.forename: Cong-Shuai
authors.initials: CS
authors.lastname: Wang
authors.forename: Ren-Yi
authors.initials: RY
authors.lastname: Zhu
authors.forename: Jian
authors.initials: J
authors.lastname: Zheng
authors.forename: Feng
authors.initials: F
authors.lastname: Shi
authors.forename: Shu-Jiang
authors.initials: SJ
authors.lastname: Tu
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000466:Alkadienes; D000480:Alkynes; D007211:Indoles; D011758:Pyrroles; C000599576:spiro(indoline-3,2'-pyrrole); C025947:propadiene