Photodecarboxylative benzylations of phthalimides

Photoadditions of phenylacetates to phthalimides give the corresponding benzylated hydroxyphthalimidines in moderate to high yields of 29–90%. With 2-phenylpropanoate, photoaddition affords a diastereoisomeric mixture in a de of 24% in favour of the like-diastereoisomer. l-3-Phenyllactate and 2-oxo-...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2009-11, Vol.50 (46), p.6335-6338
Main Authors: Hatoum, Fadi, Gallagher, Sonia, Baragwanath, Louise, Lex, Johann, Oelgemöller, Michael
Format: Article
Language:English
Subjects:
Benzylation
Photochemistry
Photodecarboxylation
Photoinduced electron transfer
Phthalimides
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Photoadditions of phenylacetates to phthalimides give the corresponding benzylated hydroxyphthalimidines in moderate to high yields of 29–90%. With 2-phenylpropanoate, photoaddition affords a diastereoisomeric mixture in a de of 24% in favour of the like-diastereoisomer. l-3-Phenyllactate and 2-oxo-3-phenylpropanoate both furnish the benzylated product through subsequent loss of formaldehyde and decarbonylation, respectively. Photoadditions of phenylacetates to phthalimides give the corresponding benzylated hydroxyphthalimidines in moderate to high yields of 29–90%. With 2-phenylpropanoate, photoaddition affords a diastereoisomeric mixture in a de of 24% in favour of the like-diastereoisomer. l-3-Phenyl lactate and 2-oxo-3-phenylpropanoate both furnish the benzylated product through subsequent loss of formaldehyde and decarbonylation, respectively.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2009.08.115