26845-57-8

Upstream product

• 26845-56-7 4-(3-bromopropyl)cyclohexanone 
• 60739-53-9 4-(tetrahydro-2H-pyran-2-yloxy)cyclohexanone 
• 26845-54-5 3-(1,4-dioxa-spiro[4.5]dec-8-yl)-propan-1-ol 
• 20498-05-9 3-allylcyclohexanone 
• 934821-86-0 4-(tetrahydropyran-2-yloxy)cyclohexanemethanol 
• 64230-40-6 4-(2-Tetrahydropyranyloxy)-1-cyclohexanol 
• 556-48-9 1,4-Cyclohexanediol 
• 211995-75-4 4-methylene-1-(tetrahydropyran-2-yloxy)cyclohexane 

Downstream Products

• 86437-33-4 (R)-2-Benzyl-3-oxa-2-aza-tricyclo[5.2.2.0^1,5]undecane 

Relevant academic research and scientific papers

Carbonyl 1,2-transposition through triflate-mediated a-amination

To date, it remains challenging to selectively migrate a carbonyl oxygen within a given molecular scaffold, especially to an adjacent carbon. In this work, we describe a simple one- or two-pot protocol that transposes a ketone to the vicinal carbon. This approach first converts the ketone to the corresponding alkenyl triflate, which can then undergo the palladium- and norbornene-catalyzed regioselective a-amination and ipso-hydrogenation enabled by a bifunctional hydrogen and nitrogen donor. The resulting "transposed enamine" intermediate can subsequently be hydrolyzed to produce the 1,2-carbonyl-migrated product. This method allows rapid access to unusual bioactive analogs through late-stage functionalization.

Intramolecular Cyclization of 4-[3-(Trimethylsilyl)prop-1-en-1-yI]-cyclohexanecarbaldehyde with Loss of Formyl Carbon

Treatment of cis- and trans-4-[3-(trimethylsilyl)prop-1-en-1-yl]cydohexanecarbaldehyde (2a and 2b) with tetrabutylammonium fluoride in dilute tetrahydrofuran afforded 7-vinylbicyclo(2.2.1]heptan-1-ol (3), the same product obtained from 4-[3-(trimethylsilyl)prop-1-en-1-yl]cyclohexanone (1). It was found that oxidative deformyhition of 2a, b to 1 takes place under basic conditions before the cyclization to 3. It was also shown that cyclization of allylsilane with carbonyl does not proceed via an eclipsed conformation.