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Asymmetric Copper‐Catalyzed Vinylogous Mukaiyama Michael Addition of Cyclic Dienol Silanes to Unsaturated α‐Keto Phosphonates |
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| Authors: | Anne‐Dorothee Steinkamp Marcus Frings Dr. Isabelle Thomé Dr. Ingo Schiffers Prof. Dr. Carsten Bolm |
| Affiliation: | 1. Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52056 Aachen (Germany);2. New address: The Scripps Research Institute, 10550 North Torrey Pines, La Jolla, CA 92037 (USA) |
| Abstract: | A highly stereoselective vinylogous Mukaiyama Michael reaction (VMMR) leading to α‐keto phosphonate‐containing γ‐butenolides with two stereogenic centers is described. The presented transformation is catalyzed by a combination of a commercially available C2‐symmetric bisoxazoline (BOX) ligand and a copper salt and tolerates a variety of nucleophiles and electrophiles. The stereoselectivities of the reactions are good to excellent and the products are obtained in moderate to high yields. |
| Keywords: | α ‐keto phosphonates asymmetric catalysis bisoxazolines copper vinylogous Mukaiyama Michael addition |