Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
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Diastereoselective Synthesis of Unsaturated 1,4-Amino Alcohols as a Biologically Important Moiety

  • Jung Young Hoon (Organic & Medicinal Chemistry Laboratory, College of Pharmacy, Sungkyunkwan University) ;
  • Kim Ji Duck (Organic & Medicinal Chemistry Laboratory, College of Pharmacy, Sungkyunkwan University)
  • Published : 2005.04.01
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Abstract

chial allylic ethers with a hydroxyl group attached to the $\pi-system$ and chlorosulfonyl isocyanate. The enantioselectivity of the CSI reaction with the chiral allylic and benzylic ethers was examined in various solvents and temperatures. Based on these results, it was proposed that the CSI reaction is a competitive reaction of a $S_{N}i$ (retention) and a $S_{N}1$ mechanism (racemization) according to the stability of the carbocation intermediate. This means that there is a greater proportion of retention with the less stable the carbocation intermediate and vise versa.

Keywords

References

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