Selective palladium-catalyzed functionalization of ?-methylene butanolides

We describe an efficient and selective functionalization of a-methylene-y-butyrolactone. The two-step sequence involves the preparation of bromomethylene butyrolactone 2 in good yield prior to a palladium-catalyzed coupling process. The latter allowed the installation of aryl, alkenyl, and alkynyl g...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron Vol. 122
Main Authors Talbi, Arbia, Arfaoui, Aicha, Efrit, Mohamed Lotfi, Gaucher, Anne, M'Rabet, Hedi, Prim, Damien
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 10.09.2022
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
NORDITERPENOIDS
CROSS-METATHESIS
SUBSTITUTED ALPHA
Palladium
GAMMA-BUTYROLACTONES
TUMOR INHIBITORS
Butenolide
LACTONES
Butyrolactone
STEREOSELECTIVE-SYNTHESIS
HECK REACTION
CYTOTOXICITY
CONSTITUENTS
Online AccessGet full text

Cover

More Information
Summary:We describe an efficient and selective functionalization of a-methylene-y-butyrolactone. The two-step sequence involves the preparation of bromomethylene butyrolactone 2 in good yield prior to a palladium-catalyzed coupling process. The latter allowed the installation of aryl, alkenyl, and alkynyl groups under Suzuki-Miyaura, Heck, and Sonogashira cross-coupling conditions. The reaction sequences involving Pd(dppf)Cl-2-CsF, Pd(OAc)(2)-PPh3-Ag2CO3, Pd(PPh4)(4)-CuI-Et3N as the corresponding catalytic systems allow the preparation of an unprecedented panel of a-unsaturated substituted butyrolactones 4 -16 ranging from moderate to excellent yields. In all cases, the E-configuration of the exo-double bond is retained from the starting materials to the targets, regardless of the nature of the substituent introduced. (C) 2022 Elsevier Ltd. All rights reserved.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2022.132926