911213-97-3

Upstream product

• 350605-86-6 2-(3-chloropropyl)-2-methylcyclohexane-1,3-dione 
• 504-02-9 1,3-cylohexanedione 
• 1193-55-1 2-methylcyclohexane-1,3-dione 
• 31929-07-4 2-allyl-2-methyl-1,3-cyclohexanedione 
• 350605-30-0 2-(3-iodopropyl)-2-methylcyclohexane-1,3-dione 

Relevant academic research and scientific papers

Overcoming product inhibition in catalysis of the intramolecular Schmidt reaction

A method for carrying out the intramolecular Schmidt reaction of alkyl azides and ketones using a substoichiometric amount of catalyst is reported. Following extensive screening, the use of the strong hydrogen-bond-donating solvent hexafluoro-2-propanol was found to be consistent with low catalyst loadings, which ranged from 2.5 mol % for favorable substrates to 25 mol % for more difficult cases. Reaction optimization, broad substrate scope, and preliminary mechanistic studies of this improved version of the reaction are described.

Asymmetric aza-Wittig reactions: Enantioselective synthesis of β-quaternary azacycles

A hindrance no more: The direct asymmetric synthesis of nitrogen heterocycles containing β-quaternary stereocenters, widely found for example in alkaloids, is highly challenging. The novel approach shown exploits the desymmetrization of prochiral diketo azides to unmask the asymmetric quaternary center, and represents the first reported examples of the asymmetric aza-Wittig reaction. (Chemical Equation Presented).

Concise access to indolizidine and pyrroloazepine skeleta via intramolecular Schmidt reactions of azido 1,3-diketones

Readily prepared 2-alkyl-2-azidopropylcycloalkyl-1,3-diones undergo intramolecular Schmidt rearrangement with a range of hard Lewis acids, leading to indolizidinediones and pyrroloazepinediones. Chiral aluminium-based Lewis acids could also be used to mediate this symmetry-breaking transformation, but no significant asymmetric induction was observed. The Royal Society of Chemistry 2006.