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Synthesis of [2.2]Paracyclophane‐Based Glycidic Amides Using Chiral Ammonium Ylides
Author(s) -
Weinzierl David,
Waser Mario
Publication year - 2021
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.202100073
Subject(s) - chemistry , ylide , kinetic resolution , epoxide , ammonium , enantioselective synthesis , stereoselectivity , aldehyde , organic chemistry , stereochemistry , catalysis
An ammonium ylide‐mediated stereoselective protocol for the synthesis of a series of novel [2.2]paracyclophane‐based epoxides starting from racemic 4‐formyl[2.2]paracyclophane has been developed. By using achiral ammonium salts as ylide precursors, the corresponding epoxide products were obtained in isolated yields up to 76 % and with diastereoselectivities up to d.r.=9 : 1. When carrying out the reaction with chiral ammonium salts instead, the products were accessible with e.r.>93.5 : 6.5 and d.r.>3 : 1, accompanied with a moderately enantioselective kinetic resolution of the racemic starting aldehyde (e.r.=75 : 25).