Construction of thiochroman-4-ols through a (4 + 2) annulation strategy using allenyl sulfones as substrates
Abstract
Herein, we report an efficient and straightforward access to highly functionalized thiochroman-4-ol derivatives by the construction of S−C and C−C bonds in a domino fashion. The methodology is based on a (4 + 2) annulation reaction involving α- substituted allenyl sulfones and aromatic thiolates displaying an ortho α-ketoester group as substrates. The anionic sulfur species were generated in situ by reduction of the corresponding disulfides, using a Rongalite/K2CO3 system. The practicality of the strategy was further demonstrated by gram-scale synthesis, postmodifications, and compatibility with other types of electron-deficient allenes (allenoate and allenone).
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