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.
作者信息
Singh Om V, Han Hyunsoo
机构信息
Department of Chemistry, The University of Texas at San Antonio, San Antonio, Texas 78249, USA.
出版信息
Tetrahedron Lett. 2007;48(13):2345-2348. doi: 10.1016/j.tetlet.2007.01.145.
Abstract
The S(N)2' 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 S(N)2' reaction, coupled with regioselective asymmetric aminohydroxylation reaction, provided a highly efficient route for the asymmetric synthesis of D-threo-N-acetylsphingosine.
摘要
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