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Substituent and Lewis Acid Promoted Dual Behavior of Epoxides towards [3+2]‐Annulation Reactions with Donor‐Acceptor Cyclopropanes: Synthesis of Substituted Cyclopentane and Tetrahydrofuran
Author(s) -
Pandey Ashok Kumar,
Varshnaya Rohit Kumar,
Banerjee Prabal
Publication year - 2017
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.201601549
Subject(s) - cyclopentane , chemistry , annulation , cyclopentene , substituent , cyclopentanone , tetrahydrofuran , lewis acids and bases , diastereomer , medicinal chemistry , organic chemistry , stereochemistry , catalysis , solvent
Substituent and Lewis acid promoted generation of functionalized enolates from epoxides is developed. Divergent attack of the enolate on donor‐acceptor cyclopropanes, i.e. C ‐attack or O ‐attack depending upon substituents present in both reacting partners, produced different products. C ‐attack gave functionalized cyclopentane derivatives, whereas O ‐attack furnished tetrahydrofuran derivatives through [3+2]‐annulation reactions. Moreover, to increase the utility of our method, synthesized diastereomeric cyclopentane derivatives were converted into synthetically useful cyclopentene and cyclopentanone analogs.