A facile one-pot stereoselective synthesis of trisubstituted (E)-2-methylalk-2-enoic acids from unactivated Baylis-Hillman adducts and a simple access to some important insect pheromones |
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Authors: | Biswanath Das Nikhil Chowdhury Joydeep Banerjee Anjoy Majhi |
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Affiliation: | Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad 500 007, India |
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Abstract: | An efficient one-pot stereoselective synthesis of trisubstituted (E)-2-methylalk-2-enoic acids has been accomplished by treatment of unactivated Baylis-Hillman adducts, 3-hydroxy-2-methylenealkanoates, with Al-NiCl2·6H2O in methanol at room temperature followed by hydrolysis. The method has been applied to the synthesis of three important insect pheromones, (4S,2E)-2,4-dimethyl-2-hexenoic acid, (+)-(S)-manicone and (+)-(S)-normanicone. |
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Keywords: | Baylis-Hillman adduct Al-NiCl2· 6H2O (E)-2-Methylalk-2-enoic acid Stereoselectivity Pheromone |
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