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Stereoselective Arene‐Forming Aldol Condensation: Synthesis of Configurationally Stable Oligo‐1,2‐naphthylenes
Author(s) -
Lotter Dominik,
Neuburger Markus,
Rickhaus Michel,
Häussinger Daniel,
Sparr Christof
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201510259
Subject(s) - stereoselectivity , aldol condensation , condensation , chemistry , aldol reaction , stereochemistry , organic chemistry , catalysis , physics , thermodynamics
Structurally well‐defined oligomers are fundamental for the functionality of natural molecular systems and key for the design of synthetic counterparts. Herein, we describe a strategy for the efficient synthesis of individual stereoisomers of 1,2‐naphthylene oligomers by iterative building block additions and consecutive stereoselective arene‐forming aldol condensation reactions. The catalyst‐controlled atropoenantioselective and the substrate‐controlled atropodiastereoselective aldol condensation reaction provide structurally distinct ter‐ and quaternaphthalene stereoisomers, which represent configurationally stable analogues of otherwise stereodynamic, helically shaped ortho‐phenylenes.