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Desymmetrization of metallated cyclohexadienes with chiral N-tert-butanesulfinyl imines

, : Desymmetrization of metallated cyclohexadienes with chiral N-tert-butanesulfinyl imines. Organic Letters 10(9): 1847-1850

This communication describes the desymmetrization of various achiral metallated cyclohexadienes with a series of chiral N-tert-butanesulfinyl imines. Depending on the metal used, either the symmetrical diene (dicyclohexadienyl-zinc) or the desymmetrized diene (cyclohexadienyl-MgCl) is obtained in a good regioselectivity with excellent diastereoselectivity. The products formed should be useful building blocks for natural product synthesis. The symmetrical 1,4-dienes are readily oxidized to the corresponding diarylmethylamine derivatives.


PMID: 18396894

DOI: 10.1021/ol800478q

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