Catalyst-Dependent Stereospecific [3,3]-Sigmatropic Rearrangement of Sulfoxide-Ynamides: Divergent Synthesis of Chiral Medium-Sized N,S-Heterocycles was written by Zhu, Guang-Yu;Zhou, Ji-Jia;Liu, Li-Gao;Li, Xiao;Zhu, Xin-Qi;Lu, Xin;Zhou, Jin-Mei;Ye, Long-Wu. And the article was included in Angewandte Chemie, International Edition in 2022.SDS of cas: 2216-51-5 This article mentions the following:
Medium-sized N,S-heterocycles have received tremendous interest due to their biol. activities and potential medical applications. However, asym. synthesis of these compounds are extremely rare. Described herein is a catalyst-dependent [3,3]-sigmatropic rearrangement of sulfoxide-ynamides, enabling divergent and atom-economic synthesis of a series of valuable medium-sized N,S-heterocycles in moderate to good yields with broad substrate scope. Importantly, excellent enantioselectivities have been achieved via an unprecedented chirality-transfer. Moreover, theor. calculations are employed to elucidate the origins of the catalyst-dependent stereospecific [3,3]-rearrangement. In the experiment, the researchers used many compounds, for example, (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5SDS of cas: 2216-51-5).
(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Converting an alcohol to an alkene requires removal of the hydroxyl group and a hydrogen atom on the neighbouring carbon atom. Dehydrations are most commonly carried out by warming the alcohol in the presence of a strong dehydrating acid, such as concentrated sulfuric acid.SDS of cas: 2216-51-5
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts