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Asymmetric Synthesis of Triaryl-Substituted Chromans with Multiple Stereogenic Centers by [4+2] Cycloaddition Reaction

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(2019)

Jilin Univ

Cited 20|Views6
Abstract
Asymmetric synthesis of triaryl‐substituted chromans with multiple adjacent stereogenic centers is described here. [4+2] formal oxa‐Diels‐Alder cycloaddition of 1‐styrylnaphthols and in‐situ‐generated o‐quinone metheides could proceed smoothly in the presence of H8‐BINOL‐type chiral imidodiphosphoric acids as catalyst. This method provides an efficient strategy to construct chiral chroman frameworks in high yields (up to 93 %) with excellent stereoselectivities (> 19:1 dr.) and enantioselectivities (up to 99 % ee).
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Key words
Enantioselective,Chromans,O-Quinone Metheides,1-Styrylnaphthols,Chiral Imidodiphosphoric Acids
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