Enantioselective Synthesis of Cyclobutylboronates via a Copper‐Catalyzed Desymmetrization Approach

Abstract

Esta es la versión de autor del artículo publicado en: This is an author produced version of a paper published in:Angewandte Chemie 128.19 (2016) El acceso a la versión del editor puede requerir la suscripción del recurso Access to the published version may require subscription

Beyond Carbon: Enantioselective and Enantiospecific Reactions with Catalytically Generated Boryl- and Silylcopper Intermediates

“…However, quantum-chemical calculations and experimental investigations have suggested that the migratory insertion of an internal double bond into Cu–B/Si bonds likely proceeds with a syn stereochemistry, resulting in the formation of the alkylcopper species IX/X . 64 − 70 This also rationalizes the stereochemical outcome of borylative amination and arylation reactions later presented in section 4 . 70 , 130 , 131 …”

Enantioselective Synthesis of Cyclobutenes by Intermolecular [2+2] Cycloaddition with Non-C2 Symmetric Digold Catalysts

“…The gold(I)-catalyzed reaction of terminal alkynes 1 with alkenes 2 leads to cyclobutenes 3 by a [2+2] cycloaddition ( Scheme 1 ), 6 which are valuable synthons for the preparation of functionalized cyclobutanes, 7 , 8 present in a variety of natural products 9 and pharmaceuticals. 10 …”

Catalytic Enantioselective Arylboration of Alkenylarenes

“…Finally, it should be noted that in all cases the products were generated as a single diastereomer (>20:1 d.r.). Additionally, strained alkenes could also be used to provide 15 and 16 …”