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Asymmetric Cross [10+2] Cycloadditions of 2‐Alkylidene‐1‐indanones and Activated Alkenes under Phase‐Transfer Catalysis
Author(s) -
Yang Yang,
Jiang Ying,
Du Wei,
Chen YingChun
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201904930
Subject(s) - cycloaddition , synthon , catalysis , chemistry , phase (matter) , combinatorial chemistry , organic chemistry
Isobenzofulvene species are versatile synthons in organic chemistry, which have been employed in diverse challenging higher‐order cycloaddition reactions. Here, the first chemoselective and asymmetric cross [10+2] cycloaddition reaction between activated 2‐alkylidene‐1‐indanones and a variety of electron‐deficient alkenes has been developed, relying on the in situ generation of dearomative 1‐hydroxyl isobenzofulvene anion intermediates under the catalysis of a newly designed bulky cinchona‐derived phase‐transfer compound. An array of fused frameworks with multifunctionalities were generally furnished in excellent diastereo‐ and enantioselectivity, even at 1 mol % catalyst loadings.