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Catalytic asymmetric 1,2‐Addition/Lactonization tandem reactions for the syntheses of chiral 3‐Substituted phthalides using organozinc reagents
Author(s) -
Huang Huayin,
Wang Yabai,
Zong Hua,
Song Ling
Publication year - 2019
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.4643
Subject(s) - chemistry , reagent , catalysis , tandem , aryl , ligand (biochemistry) , alkyl , combinatorial chemistry , chiral ligand , organic chemistry , enantioselective synthesis , optically active , medicinal chemistry , receptor , biochemistry , materials science , composite material
Using chiral phosphoramide ligand 2d‐ Zn (II) complex derived from (1 R ,2 R )‐1,2‐diphenylethylenediamine as the catalyst, we have developed efficient catalytic asymmetric 1,2‐addition/lactonization tandem reactions of diverse organozinc reagents with varied methyl 2‐formylbenzoates for the construction of optically enriched 3‐aryl or alkyl substituted phthalides, which are significant building blocks of many important chiral pharmaceuticals and natural products. The corresponding products could be afforded with good to excellent yields (up to 95%) and moderate to good enantioselectivities (up to 89%).