The [2,3]-sigmatropic rearrangement of sulfonium ylides bearing substituted allyl groups creates two contiguous stereocentres. Low diastereoselectivity is typically observed from commonly used α-diazocarboxylic ester precursors. High diastereoselectivity was previously revealed in a gold-catalyzed multicomponent route into allyl sulfonium ylides by reaction of ynamide, oxidant and allyl sulfides. The effect of substrate modifications on the diastereoselectivity have been studied, with N-phenyl methanesulfonamide derived ynamides proving the most effective. This report includes an enhanced experimental procedure, and a demonstration that the gold-catalyzed process remains highly effective at −78 °C.

带有取代的烯丙基的的[2,3]-σ重排产生两个连续的立体中心。通常从常用的α-重氮羧酸酯前体中观察到低的非对映选择性。先前通过金催化的多组分途径，通过乙酰胺，氧化剂和烯丙基硫的反应，揭示出高非对映选择性，形成烯丙基sulf的烷基化物。已经研究了底物修饰对非对映选择性的影响，其中N-苯基甲磺酰胺衍生的酰胺被证明是最有效的。该报告包括改进的实验程序，并论证了金催化的过程在-78°C下仍然非常有效。