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α‐Arylation and Ring Expansion of Annulated Cyclobutanones: Stereoselective Synthesis of Functionalized Tetralones
Author(s) -
Chang Stanley,
Holmes Michael,
Mowat Jeffrey,
Meanwell Michael,
Britton Robert
Publication year - 2017
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.201608449
Subject(s) - tetralones , stereoselectivity , chemistry , ring (chemistry) , reactivity (psychology) , aldol reaction , aryl , combinatorial chemistry , molecule , stereochemistry , organic chemistry , catalysis , medicine , alkyl , alternative medicine , pathology
α‐Arylcyclobutanones display unique reactivity that makes them valuable synthetic intermediates and target molecules. We describe the preparation of α‐aryl‐ and α‐heteroarylcyclobutanones through a direct α‐arylation reaction. Problematic fragmentations are avoided by the use of LiO t Bu, which promotes a rapid but reversible self‐aldol reaction that slowly releases the enolate required for α‐arylation. We also demonstrate the ring expansion of α‐arylcyclobutanones, a process that is highlighted in the stereoselective synthesis of 1‐methoxy coniothyrinone D.