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Tuning the Structure of Phosphahelicenes for Targeted Applications in Enantioselective Phosphine Organocatalysis
Author(s) -
Aillard Paul,
Gicquel Maxime,
Yavari Keihann,
Retailleau Pascal,
Voituriez Arnaud,
Marinetti Angela
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800438
Subject(s) - enantioselective synthesis , chemistry , halogenation , phosphine , organocatalysis , combinatorial chemistry , nucleophile , organic chemistry , catalysis , stereochemistry
The use of phosphahelicenes as nucleophilic organocatalysts for [3+2] cyclization reactions between allenoates and 2‐benzylidenemalononitriles has been extended by the systematic screening of phosphines with different helical scaffolds and substitution patterns. Among others, a new series of phosphahelicenes have been prepared by bromination/Suzuki coupling reactions of a pre‐formed phosphahelicene. This late bromination approach represents a suitable strategy for accessing a broad variety of substituted phosphahelicenes from a single intermediate. It represents a powerful tool for the catalysis‐oriented optimization of their structural features.