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Chiral acetylene thioethers: Synthesis and Pauson-Khand reactions

, : Chiral acetylene thioethers: Synthesis and Pauson-Khand reactions. Tetrahedron 53(25): 8651-8664

Chiral acetylene thioethers have been prepared in excellent yields from the corresponding thiols. The procedure involves the treatment of the corresponding thiolate with 2-bromo-1,1-diethoxyethane followed by double elimination with LDA and, in some cases, alkylation of the acetylide with alkyl or omega-alkenyl iodides. These compounds have been tested in both intra- and intermolecular Pauson-Khand reactions. This study clearly shows that acetylenic thioethers can be excellent substrates for asymmetric versions of this reaction.


DOI: 10.1016/s0040-4020(97)00535-8

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