Stereoselective synthesis of (R)-10-methyltridecan-2-one,the sex pheromone of the southern corn rootworm,using (4S)-benzylthiazolidinethione as a chiral auxiliary |
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| Authors: | Cui-Fen Lu Shou-Bo Zhang Yan Li Gui-Chun Yang Zu-Xing Chen |
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| Institution: | Ministry-of-Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules and School of Chemistry and Chemical Engineering, Hubei University, Wuhan 430062, China |
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| Abstract: | The stereoselective synthesis of (R)-10-methyltridecan-2-one, the sex pheromone of the southern corn rootworm, was carried out in 20.7% overall yield based on (4S)-benzylthiazolidinethione (five steps). In the crucial step, the stereogenic center was generated by an asymmetric Michael addition using enantiomerically pure (4S)-benzylthiazolidinethione as a chiral auxiliary. |
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