Stereoselective synthesis of alicyclic ketones: a hydrogen borrowing approach

Stereoselective synthesis of alicyclic ketones: a hydrogen borrowing approach

A highly diastereoselective annulation strategy for the synthesis of alicyclic ketones from diols and pentamethylacetophenone is described. This process is mediated by a commercially available iridium(III) catalyst, and provides efficient access to a wide range of cyclopentane and cyclohexane produc...

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Hlavní autoři: Armstrong, RJ, Akhtar, WM, Frost, JR, Christensen, KE, Stevenson, NG, Donohoe, TJ
Médium: Journal article
Jazyk:English
Vydáno: Elsevier 2019
Popis
Shrnutí:A highly diastereoselective annulation strategy for the synthesis of alicyclic ketones from diols and pentamethylacetophenone is described. This process is mediated by a commercially available iridium(III) catalyst, and provides efficient access to a wide range of cyclopentane and cyclohexane products with high levels of stereoselectivity. The origins of diastereoselectivity in the annulation reaction have been explored by a series of control experiments, which provides an explanation for how each stereocentre around the newly forged ring is controlled.

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