The asymmetric synthesis of (S)-2-sec-butyl-4,5-dihydrothiazole, one of the pheromone components of the male mouse, Mus musculus, has been achieved by induction of chirality through stereoselective alkylation reaction using non-cross-linked polystyrene (NCPS) supported 2-phenylimino-2-oxazolidine as a chiral auxiliary. This method is efficient, and the chiral auxiliary can be recovered by simple filtration. The final product was obtained in 91% ee and 23% overall yield.
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Acknowledgment
This work is supported by the National Natural Sciences Foundation of China (Nos. 20772026 and 21042005) and the Natural Sciences Foundation of Hubei Province in China (No. 2010CDA019).
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Published in Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2012, pp. 765–767.
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Lu, C.F., Hu, F.Q., Yang, G.C. et al. Asymmetric synthesis of (S)-2-sec-Butyl-4,5-dihydrothiazole, a pheromone component of the Mus musculus . Chem Nat Compd 48, 860–862 (2012). https://doi.org/10.1007/s10600-012-0401-3
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DOI: https://doi.org/10.1007/s10600-012-0401-3