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Switchable Skeletal Rearrangement of Dihydroisobenzofuran Acetals with Indoles
Guofeng Li1, Ying Yao1, Zheng Wang2
1Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences , Sun Yat-sen University , Guangzhou 510006 , China.
Abstract:
The switchable skeletal rearrangement for the construction of amino indanones and tetrahydroisoquinolones frameworks had been developed. In the presence of a chiral phosphoric acid catalyst, the reaction gave the amino indanones in high yields and good to excellent ee (85-98%), while the methoxyl substituent at the 5-position of dihydroisobenzofuran acetal selectively gave isoquinolinones products in good to excellent ee (46-98%). Furthermore, DFT calculations were performed to explain the regioselectivity of the switchable transformation pathways.
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