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Photocycloaddition of Phthalimide Anion to Alkenes − A Highly Efficient, Convergent Method for [2]Benzazepine Synthesis
Author(s) -
Suau Rafael,
SánchezSánchez Cristóbal,
GarcíaSegura Rafael,
PérezInestrosa Ezequiel
Publication year - 2002
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 - 10.1002/1099-0690(200206)2002:12<1903::aid-ejoc1903>3.0.co;2-p
Subject(s) - chemistry , phthalimide , indene , alkene , regioselectivity , benzazepine , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , catalysis
The excited state of phthalimide anion adds to cyclic, acyclic and aryl‐conjugated alkenes in an efficient and regioselective manner to form [2]benzazepine‐1,5‐diones, substituted at positions 3 and/or 4. The reaction is independent of the ionization potential of the alkene. This process contrasts with the related reactions of N ‐methylphthalimide or phthalimide, which are limited by the requirement that the participating alkenes have oxidation potentials > ca. 2 V. Photocycloaddition of the phthalimide anion with indene serves as a concise method to prepare the basic skeleton found in members of the ribasine alkaloid family. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)