A diastereoselective [4 + 2]-annulation of vinyl carbodiimides with chiral N-alkyl imines has been developed to access the stereochemically rich polycyclic guanidine cores of the batzelladine alkaloids. Application of this strategy, together with additional key steps such as long-range directed hydrogenation and diastereoselective intramolecular iodo-amination, led to highly convergent total syntheses of (-)-batzelladine D and (+)-batzelladine A with excellent stereocontrol.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2610335 | PMC |
| http://dx.doi.org/10.1021/ja063860+ | DOI Listing |
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Enantioselective Synthesis of Cyclopentenes by (3+2) Annulation via a 2-Carbon Phosphonium.
Angew Chem Int Ed Engl
August 2024
School of Chemistry, Monash University, Clayton, 3800, Victoria, Australia.
Herein we report a catalytic enantioselective (3+2) annulation, in which a vinyl phosphonium intermediate serves as the 2-carbon component. The reaction involves an α-umpolung β-umpolung coupling sequence, enabled by β-haloacrylates and chiral enantioenriched phosphepine catalysts. The reaction shows good generality, providing access to an array of cyclopentenes, with mechanistic studies supporting stereospecific formation of the vinyl phosphonium intermediate which, then undergoes annulation with turn over limiting catalyst elimination.
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