Abstract
AbstractThe diastereoselective synthesis of 6‐aroyl‐3,5‐diarylspiro[cyclohexa‐2,4‐diene‐1,2′‐indolines] 4 possessing three stereocenters from 2,4,6‐triarylpyrylium perchlorates 1 and chiral methyleneindolines 3 (generated in situ by deprotonation of the corresponding 3H‐indolium perchlorates 2) in the presence of triethylamine/acetic acid in ethanol by a 2,5‐[C4+C2] pyrylium ring transformation is reported. Structure elucidation is performed by X‐ray structure determinations of the spiro[cyclohexadiene‐indolines] 4a, 4p and 4t. The influence of various substituents at C‐3 of the methyleneindolines 3 on the stereochemistry of the transformation, mechanistic details as well as spectroscopic data of the products 4 are discussed.
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