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Regiodivergent Cyclobutanone Cleavage: Switching Selectivity with Different Lewis Acids
Author(s) -
Souillart Laetitia,
Cramer Nicolai
Publication year - 2015
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.201406135
Subject(s) - cyclobutanone , lewis acids and bases , regioselectivity , cleavage (geology) , chemistry , selectivity , bond cleavage , combinatorial chemistry , stereochemistry , catalysis , organic chemistry , ring (chemistry) , materials science , fracture (geology) , composite material
The exploitation of strain release in small rings as driving force to enable complex transformations is a powerful synthetic tool. Among them, cyclobutanones are particularly versatile substrates that can be elaborated in a wide variety of structurally diverse building blocks. Herein, Lewis acid catalyzed rearrangement reactions are presented that provide selective access to two structurally distinct polycyclic scaffolds, that is, indenylacetic acid derivatives and benzoxabicyclo[3.2.1]octan‐3‐ones. The choice of the Lewis acid fully controls the reaction pathway and the regioselectivity of the cyclobutanone CC bond cleavage site.