Abstract
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.
Highlights
Reactions were carried out in flame-dried glassware under an atmosphere of nitrogen unless stated otherwise
Electron impact ionisation (EI) HRMS were performed on an Agilent 7200 quadrupole time of flight (Q-ToF) instrument equipped with a direct insertion probe supplied by Scientific Instrument Manufacturer (SIM) GmbH
Chiral HPLC was performed on an Agilent 1260 Series HPLC unit equipped with UV-vis diode-array detector fitted with the appropriate Daicel Chiralpak column along with the corresponding guard column (0.4 cm ø x 1 cm)
Summary
Reactions were carried out in flame-dried glassware under an atmosphere of nitrogen unless stated otherwise. Temperatures of 0 °C were obtained using an ice/water bath. Temperatures of –17 °C were obtained using a salt/ice bath. Temperatures of –78 °C were obtained using a dry ice/acetone bath. Electrospray ionisation (ESI) HRMS were recorded on a Thermo Exactive orbitrap spectrometer equipped with a Waters Equity LC system, with a flow rate of 0.2 mL/min using. The mass reported is that containing the most abundant isotopes, with each value rounded to 4 decimal places and within 5 ppm of the calculated mass. Electron impact ionisation (EI) HRMS were performed on an Agilent 7200 quadrupole time of flight (Q-ToF) instrument equipped with a direct insertion probe supplied by Scientific Instrument Manufacturer (SIM) GmbH. The mass reported is that containing the most abundant isotopes, with each value to 4 decimal places and within 5 ppm of the calculated mass. Crystallographic data have been deposited with the Cambridge Crystallographic Data Centre (CCDC 1944075-79) and can be obtained via www. ccdc.cam.ac.uk/data_request/cif
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