3 years ago

Use of Triethylsilane for Directed Enantioselective Reduction of Olefines: Synthesis of Pyrazino[2,1-c][1,4]oxazine-6,9-diones with Full Control of the Absolute Configuration

Use of Triethylsilane for Directed Enantioselective Reduction of Olefines: Synthesis of Pyrazino[2,1-c][1,4]oxazine-6,9-diones with Full Control of the Absolute Configuration
Miroslav Soural, Veronika Ručilová, Michal Maloň
Herein, we report the use of triethylsilane for the synthesis of hexahydropyrazino[2,1-c][1,4]oxazine-6,9-diones with full control of three stereocenters. Unsaturated tetrahydropyrazino-oxazine-diones were prepared in accordance with a previously reported procedure and were treated with triethylsilane-trifluoroacetic acid. The stereoselectivity of the reduction was completely dependent on the overall conformation of the oxazine scaffold, which was a consequence of the C9 configuration of the starting material. The results prove that triethylsilane can be used for directed enantioselective syntheses of single or fused morpholine-based heterocycles.Triethylsilane-trifluoroacetic acid reduction of hexahydropyrazino[2,1-c][1,4]oxazine-6,9-diones with full control of three stereocenters is reported. The stereoselectivity is completely dependent on the overall conformation of the starting oxazine scaffold. The results prove that triethylsilane can be used for directed enantioselective syntheses of single or fused morpholine-based heterocycles.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/ejoc.201701553

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