An alternative stereoselective synthesis of the macrocyclic fragrances (R)-12-methyltridecanolide and (S)-muscolide by means of an asymmetric catalytic conjugate addition/Baeyer–Villiger oxidation |
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| Affiliation: | 1. Department of Environmental Engineering, University of Dammam, 31982 Dammam, Saudi Arabia;2. Department of Chemical Engineering, King Fahd University of Petroleum & Minerals, 31261 Dhahran, Saudi Arabia,;3. Center of Research Excellence in Nanotechnology, King Fahd University of Petroleum & Minerals, 31261 Dhahran, Saudi Arabia;1. Institut UTINAM – UMR UFC CNRS 6213, Sonochemistry and Surfaces Reactivity, Université de Franche-Comté, Besançon 25000, France;2. Chemical and Biomolecular Engineering, The University of Melbourne, VIC 3010, Australia;3. School of Chemistry, The University of Melbourne, VIC 3010, Australia;1. School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, PR China;2. College of Ordos, Inner Mongolia University, Ordos 017000, Inner Mongolia, PR China;3. Institute of Applied Chemistry, Shanxi University, Taiyuan 030006, PR China;1. State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China;2. University of Chinese Academy of Sciences, Beijing 100049, China;1. Fusion Reactor Materials Section, Bhabha Atomic Research Centre, Mumbai 400085, India;2. Analytical Chemistry Division, Bhabha Atomic Research Centre, Mumbai 400085, India;1. Pharmaceutical Research Laboratory, Department of Chemistry, Isfahan University of Technology, Isfahan 84156, Iran;2. Department of Neuroscience, University of Wisconsin, Medical School, Madison, WI 53706-1532, USA;3. Young Researchers and Elite Club, Shahreza Branch, Islamic Azad University, Shahreza, Iran |
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| Abstract: | We show herein an alternative catalytic, highly enantioselective approach to (R)-12-methyltridecanolide and (S)-muscolide, that is, chiral macrocyclic lactones which are good musk odorants. In fact, they can be efficiently prepared by a sequence of reactions consisting of a catalytic asymmetric conjugated addition of dimethylzinc to suitable α,β-unsaturated enones followed by a Baeyer–Villiger oxidation. Interestingly, high enantiomeric excesses (up to 92%) are obtained in the asymmetric conjugate addition by means of the ‘tropos’ phosphoramidite L1. |
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