Stereospecific Reactions Leading to Allylboronic Esters Within Acyclic Systems Bearing Distant Stereocenters |
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Authors: | Dr David Pierrot Prof Dr Ilan Marek |
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Institution: | Schulich Faculty of Chemistry, Technion—, Israel Institute of Technology, Technion City, 3200009 Haifa, Israel |
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Abstract: | The preparation of acyclic molecules featuring congested stereocenters in a 1,4-relationship in only three catalytic steps from commercially available building blocks is reported. This approach involves a diastereoselective diboration of alkenyl cyclopropyl methanol derivatives followed by a regioselective exergonic ring fragmentation. The starting materials can be prepared enantiomerically enriched and all substituents can be interconverted, therefore, this strategy allows a large variety of diversely functionalized allylboronic esters possessing distant tetrasubstituted stereocenters with high diastereoselectivity. |
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Keywords: | alkenyl cyclopropyl methanol allylboronic esters diboration fragmentation stereocenters |
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