Catalytic asymmetric 1,2 ‐Addition/Lactonization tandem reactions for the syntheses of chiral 3‐Substituted phthalides using organozinc reagents

Using chiral phosphoramide ligand2d ‐Zn (II) complex derived from (1R,2R) ‐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%). Using chiral phosphoramide ligand2d ‐Zn (II) complex derived from (1R,2R) ‐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%).

Source: Applied Organometallic Chemistry - October 18, 2018 Category: Chemistry Authors: Huayin Huang, Yabai Wang, Hua Zong, Ling Song Tags: FULL PAPER Source Type: research