Asymmetric synthesis of functionalized 2,3-dihydrobenzofurans using salicyl: N -phosphonyl imines facilitated by group-assisted purification (GAP) chemistry

Hossein Rouh, Yao Tang, Sai Zhang, Ahmed I.M. Ali, Daniel Unruh, Kazimierz Surowiec, Guigen Li

Abstract

In this work, we present a strategy for the preparation of functionalized 2,3-dihydrobenzofuran derivatives via the Cs2CO3-catalyzed domino annulation of enantiopure chiral salicyl N-phosphonyl imines with bromo malonates, which offers an avenue for the construction of 2,3-dihydrobenzofurans. Nineteen examples were synthesized in impressive chemical yields and diastereoselectivity. The products were purified simply by washing the crude mixtures with hexanes following group-assisted purification chemistry/technology to bypass traditional separation methods which often result in a loss of product. The absolute configuration was unambiguously assigned by X-ray structural analysis. This journal is

Original languageEnglish
Pages (from-to)10319-10325
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume19
Issue number47
DOIs
StatePublished - Dec 21 2021

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