Selective palladium-catalyzed functionalization of ?-methylene butanolides

被引：0

作者：

Talbi, Arbia ^{[1
,2
]}

Arfaoui, Aicha ^{[2
]}

Efrit, Mohamed Lotfi ^{[2
]}

Gaucher, Anne ^{[1
]}

M'Rabet, Hedi ^{[2
]}

Prim, Damien ^{[1
]}

机构：

[1] Univ Paris Saclay, CNRS, Inst Lavoisier Versailles, UVSQ, F-78035 Versailles, France

[2] Univ Tunis El Manar, Fac Sci Tunis, Lab Synth Organ & Heterocycl Select Evaluat Act Bi, Campus Univ, Tunis 2092, Tunisia

来源：

TETRAHEDRON | 2022年 / 122卷

关键词：

Butyrolactone; Butenolide; Palladium; STEREOSELECTIVE-SYNTHESIS; GAMMA-BUTYROLACTONES; SUBSTITUTED ALPHA; TUMOR INHIBITORS; CROSS-METATHESIS; HECK REACTION; LACTONES; NORDITERPENOIDS; CYTOTOXICITY; CONSTITUENTS;

D O I：

10.1016/j.tet.2022.132926

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页数：5

共 31 条

[1] Palladium(II)-catalyzed enyne cyclization strategies toward the podophyllotoxin ring system [J].