Stereoselective Domino Carbocyclizations of γ- and δ-Cyano-N-tosylhydrazones with Alkenylboronic Acids with Formation of Two Different C(sp(3))-C(sp(2)) Bonds on a Quaternary Stereocenter.
J Am Chem Soc
; 138(37): 12061-4, 2016 09 21.
Article
en En
| MEDLINE
| ID: mdl-27618127
ABSTRACT
A novel strategy for the synthesis of functionalized carbocycles is defined, through the cascade carbocyclization of alkenylboronic acids with δ- or γ-cyano-N-tosylhydrazones. In the reaction, two C(sp(3))-C(sp(2)) bonds are formed on the former hydrazonic carbon generating an all-carbon quaternary stereocenter, and leading to cyclic ketones featuring an alkenyl side chain with complete diastereoselectivity. The processes are conducted under very simple experimental conditions, only in the presence of K2CO3, in 1,4-dioxane as solvent and under microwave irradiation, and have been applied for the synthesis of a wide structural variety of fused cyclopentanones and cyclohexanones. Moreover, the versatility of this methodology has been demonstrated in the structural modification of androsterone.
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Colección:
01-internacional
Banco de datos:
MEDLINE
Idioma:
En
Revista:
J Am Chem Soc
Año:
2016
Tipo del documento:
Article
País de afiliación:
España