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Carboxylates as Nucleophiles in the Enantioselective Ring‐Opening of Formylcyclopropanes under Iminium Ion Catalysis
Author(s) -
Díaz Estibaliz,
Reyes Efraim,
Uria Uxue,
Carrillo Luisa,
Tejero Tomas,
Merino Pedro,
Vicario Jose L.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201801434
Subject(s) - iminium , nucleophile , enantioselective synthesis , desymmetrization , chemistry , ring (chemistry) , catalysis , amine gas treating , reagent , organocatalysis , organic chemistry , combinatorial chemistry , medicinal chemistry , ion
Abstract In this work, carboxylic acids, which are typically regarded as poor nucleophiles, are demonstrated to be competent reagents to promote the ring‐opening of formylcyclopropanes after activation of the latter through iminium ion formation. Under optimized reaction conditions, a variety of γ‐acyloxy‐substituted aldehydes can be obtained in high yields and enantioselectivities through the desymmetrization of substituted meso ‐formylcyclopropanes in the presence of a chiral secondary amine as catalyst.