Diastereoselectivity in unusual intermolecular tandem Michael reactions |
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| Authors: | Andrew B Hughes Christopher M Verdon Jonathan M White |
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| Institution: | 1. Department of Chemistry, La Trobe Institute of Molecular Sciences, La Trobe University, Kingsbury Drive, Melbourne, Victoria 3086, Australia;2. Department of Chemistry, University of Melbourne, Parkville 3010, Australia |
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| Abstract: | Highly stereoselective consecutive or tandem Michael (MIMI) reactions are reported. A variety of initial nucleophiles react with chiral acylated 1,3-oxazolidin-2-ones to generate a reactive enolate. The enolate then reacts stereoselectively with a second equivalent of the acylated 1,3-oxazolidin-2-one to afford ‘dimeric’ adducts. The adducts have three new contiguous stereogenic centers formed with a high level of control. Single crystal X-ray crystallographic analysis confirmed this controlled formation of novel tandem acyclic conjugate addition or MIMI products in several examples. |
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