Producción Científica Profesorado

Stereoselective addition of allylmagnesium chloride to the CN bond of [4.3.0] boron heterobicycles



Rojas Lima, Susana

2008

Heraclio López-Ruiz, Ivan Mera-Moreno, Susana Rojas-Lima, Rosa Santilllán, Norberto Farfán. Stereoselctive addition of allylmagnesium chloride to the C=N bond of [4.3.0]boron heterobicycle. Tetrahedron Letters 2008, Vol. 49, Núm. 10, pp 1674-1677. DOI: http://dx.doi.org/10.1016/j.tetlet.2007.12.122


Abstract


An efficient, simple protocol for the addition of allylmagnesium chloride to the CN bond of [4.3.0] boron heterobicycles afforded five new dioxaboracyclononenes 4ae in moderate yields (5161%). The boronates were characterized by 1H, 13C, 11B and 2D NMR experiments, and confirmed by X-ray analogues. The stereochemistry of the NH, CH2CHCH2 and BPh fusion is always cis, as established through NMR, and confirmed by X-ray structure of 4d. The structure of one of the addition products was established by X-ray analysis showing that, in the solid state, it exists as a polymeric structure formed by hydrogen bonds between the amine proton and the ester oxygen of the five-membered ring.



Producto de Investigación




Artículos relacionados

3-Benzoyl-2-isopropyl-4-alkyloxazolidin-5-ones as Efficient and Inexpensive Sources of Enantiopure ?...

A practical access to acyl radicals from acyl hydrazides

Comparative Structural Characterization of the Biquaternized N-CH3 and N-BH3 Derivatives of the cis-...

Highly diastereoselective alkylation, acylation and aldol condensation of cis- and trans-(N-acyloyl)...

ChemInform Abstract: Facile Preparation of [4.4]Metacyclophane- and [5.5]Paracyclophane-Type Macrocy...

Synthesis of New Chiral Derivatives of N,N?-Dimethylpropyleneurea (DMPU) and Examination of Their In...

Synthesis and Study of Monomeric and Dimeric Boronates by Spectroscopic Methods and X-ray Crystallog...

Furocoumarins of three species of the genus Dorstenia

Et3, and efficient Mediator for Xanthate Transfer Based Radical Processes.

Phenylboronic acid catalyzed-cyanide promoted, one-pot synthesis of 2-(2-hydroxyphenyl)benzoxazole d...