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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
Author(s) -
Ručilová Veronika,
Maloň Michal,
Soural Miroslav
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701553
Subject(s) - triethylsilane , chemistry , stereocenter , enantioselective synthesis , stereoselectivity , trifluoroacetic acid , stereochemistry , absolute configuration , combinatorial chemistry , organic chemistry , catalysis
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 C 9 configuration of the starting material. The results prove that triethylsilane can be used for directed enantioselective syntheses of single or fused morpholine‐based heterocycles.