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Straightforward and Regioselective Access to Unsaturated α‐Benzyl Butyrolactones
Author(s) -
Talbi Arbia,
Bsaibess Talia,
Efrit Mohamed Lotfi,
M'Rabet Hédi,
Gaucher Anne,
Prim Damien
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.201700895
Subject(s) - chemistry , regioselectivity , combinatorial chemistry , organic chemistry , stereochemistry , catalysis
The efficient preparation of various substituted α‐benzyl unsaturated butyrolactones is described. The palladium‐mediated C–C bond formation that uses α‐bromomethylbutenolide and boron derivatives as coupling partners accounts for the key step of this synthetic approach. Our strategy exclusively affords the endocyclic adduct and represents an alternative to Heck‐type reactions. The synthesis and characterization of two nostoclide analogues has also been reported.