Copper-Catalyzed Enantioselective 1,2-Allylation of Azadienes with Allylboronates

Organic Letters, Год журнала: 2024, Номер 26(15), С. 3235 - 3240

Опубликована: Апрель 1, 2024

Catalytic asymmetric 1,2-allylation of aurone-derived azadienes is very difficult to achieve due the driving force for aromatization and greater steric hindrance 1,2-addition compared with 1,4-addition. By taking advantage ability nitrogen ligated metal complexes, we successfully demonstrated first example copper-catalyzed allylboronates highly enantioselective synthesis homoallylic amines. Meanwhile, enantioenriched 1,4-addition products could also be obtained through a subsequent 3,3-sigmatropic rearrangement products. Extensive DFT calculations were carried out elucidate origins high regioselectivity (1,2- vs 1,4-) enantioselectivity.

Язык: Английский

---

Copper-catalyzed remote double functionalization of allenynes

Chemical Science, Год журнала: 2024, Номер 15(20), С. 7789 - 7794

Опубликована: Янв. 1, 2024

A copper-catalyzed highly regioselective remote boryl- or silyl-cupration of allenynes, providing an efficient protocol for the synthesis conjugated allene-substituted alkenyl boronates silanes, has been developed.

Язык: Английский

---

Preparations of Silyl Anions

Synthesis, Год журнала: 2023, Номер 56(14), С. 2183 - 2212

Опубликована: Дек. 27, 2023

Abstract This review collates synthetic procedures for the synthesis of different silyl anions, which are valuable reagents chemists, particularly in field organic and organometallic chemistry. includes preparation anions lithium, sodium, potassium, rubidium, cesium from group I metals beryllium, magnesium, calcium, strontium, barium II metals. Synthetic zirconium, hafnium, cadmium, zinc also covered. The XIII boron aluminum is highlighted. 1 Introduction 2 Silyl Anions Group Metals 2.1 Silyllithium 2.2 Silylsodium 2.3 Silylpotassium 2.4 Silylrubidium Silylcesium 3 3.1 Silylberyllium 3.2 Silylmagnesium 3.3 Silylcalcium, -strontium, -barium 4 Transition 4.1 Silylzirconium -hafnium 4.2 Silylcopper -cuprates 4.3 Silylzinc 4.4 Disilylzinc 4.5 Silylzincate 4.6 Silylcadmium 5 Pronucleophiles 5.1 Silylboranes 5.2 Silylaluminum 6 XIV 6.1 Disilane Synthesis 7 Conclusions

Язык: Английский

---

Enantio- and Diastereoselective Copper-Catalyzed Borylative Coupling of Styrenes and Azadienes

Organic Letters, Год журнала: 2024, Номер 26(25), С. 5335 - 5340

Опубликована: Июнь 17, 2024

Here we disclose a CuB-catalyzed reaction between aurone-derived α,β-unsaturated imines and styrenes to produce 2-substituted benzofuran derivatives bearing both the γ-boryl functionality α,β-unsymmetric stereogenic centers. The represents first transition-metal-catalyzed unsymmetric 1,4-Michael additions of azadienes, which would enrich arsenal CuB catalysis in organic synthesis. In addition, synthetically versatile boron-alkylated products can be elaborated by chemical transformations useful optically active heterocycles.

Язык: Английский

---

Six-membered ring systems: Pyridines and benzo analogs

Progress in heterocyclic chemistry, Год журнала: 2024, Номер unknown, С. 309 - 354

Опубликована: Янв. 1, 2024

Язык: Английский

---