Over the past two decades, Julia‐Kocienski olefination has become one of the most powerful and reliable C=C double‐bond construction methods typically furnishing E‐configured alkenes. This review summarizes the scientific literature of the past decade focusing on the key aspects for successful execution of the olefination step. The main stereoselectivity and yield‐determining aspects have been outlined in separate chapters providing all the necessary information for the synthesis of Julia‐Kocienski reagents as well as the most commonly used reaction optimization techniques.
Total syntheses of three pyrrolo[1,4]benzodiazepine anticancer
antibiotic family members oxo-prothracarcin, oxo-tomaymycin, and boseongazepine
B are described. The total syntheses feature late-stage stereoselective
olefination employing modified Julia–Kocienski reagents that
can be conveniently prepared in only two steps and allows for a significant
reduction in the number of linear steps. Detailed density functional
theory (DFT) studies explain the stereochemical outcome of the key
step.
Asymmetric induction caused by 4-substituted oxazolidin-2-one type auxiliaries in reactions of N-cinnamoyloxazolidinones with phenylmagnesium bromide in the presence of CuBr×SMe2 catalyst were examined. Resulted 3,3-diarypropionic acid derivatives were converted into 6-hydroxy-4-phenyldihydrocoumarine via demethylation and subsequent pyrane ring closure. Hydroarylation of N-cinnamoyloxazolidinones with 1,3,5-trimethoxybenzene was performed affording 3,3-diarypropionic acid derivatives.
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