Stereoselective Synthesis of trans-Olefins by the Copper-Mediated S(N)2' Reaction of Vinyl Oxazines with Grignard Reagents. Asymmetric Synthesis of D-threo-Sphingosines |
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| Authors: | Singh Om V Han Hyunsoo |
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| Institution: | Department of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, TX 78249, USA |
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| Abstract: | The SN2′ reaction of 6-vinyl-5,6-dihydro-4H-1,3]oxazines with Grignard reagents in the presence of CuCN was studied, and high trans selectivity for the formation of double bond was observed with a variety of RMgX. The SN2′ reaction, coupled with regioselective asymmetric aminohydroxylation reaction, provided a highly efficient route for the asymmetric synthesis of d-threo-N-acetylsphingosine. |
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| Keywords: | Sphingosine Regioselective asymmetric aminohydroxylation Oxazine SN2&prime Reaction Grignard reagents |
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