178435-68-2Relevant academic research and scientific papers
Intramolecular C-H insertion reactions of boroxy Fischer carbene complexes. Regio-and diastereoselective modification of terpenes
Barluenga, Jose,Rodriguez, Felix,Vadecard, Jerome,Bendix, Maximilian,Fananas, Francisco J.,Lopez-Ortiz, Fernando,Rodriguez, Miguel A.
, p. 8776 - 8782 (2007/10/03)
In-situ-generated dialkylboroxy and diaminoboroxy Fischer carbene complexes lead to oxaborolane or oxazaborolidine derivatives via an intramolecular C-H insertion reaction. Further oxidation of these intermediates yields 1,3-diol or 1,2-amino alcohol derivatives. Diastereoselectivities as high as 99% are reached when starting from boroxy Fischer carbene complexes derived from terpenes, which represents a regio-and diastereoselective modification of this type of natural product. The influence of the Cβ substituents relative to the boron atom on the reaction path is studied, and a mechanism is proposed after identification of an intermediate by NMR. In addition, theoretical calculations show the presence of a boron-metal interaction, which could result as key step to the C-H insertion reaction.
