✍ Scribed by Nobuyoshi Morita; Norbert Krause
No coin nor oath required. For personal study only.
The use of gold catalysts in organic synthesis has received much attention in recent years because they exhibit extraordinary reactivities and selectivities in various transformations such as inter-and intramolecular addition reactions, cyclizations, cycloisomerizations, and rearrangements. [1] To date, these gold-catalyzed reactions have been utilized for the highly efficient formation of CÀC, CÀO, and CÀN bonds. In contrast, there seems to be no precedent for the formation of a carbon-sulfur bond in the presence of a gold catalyst. A rationale for this might be that organosulfur compounds such as thiols, sulfides, and disulfides are known to strongly coordinate to transition metals, especially to gold, which does not render the use of gold catalysts in the presence of these functional groups very promising. This high affinity of gold and sulfur is frequently applied in various fields, for instance in the generation of self-assembled monolayers (SAMs) [2] and the use of gold thiolates as drugs, for example, for the treatment of rheumatoid arthritis. [3] Recently, we reported the highly efficient gold-catalyzed cycloisomerization of a-hydroxyallenes to 2,5-dihydrofurans, [4] as well as of a-aminoallenes to 3-pyrrolines [5] in good to high yields with complete axis-to-center chirality transfer (that is, chirality transfer from the allenic chirality axis to the newly formed stereogenic center; Scheme 1). The heterocy-
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