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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)
Publication Information
Archives of Pharmacal Research / v.28, no.4, 2005 , pp. 382-390 More about this Journal
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
Chlorosulfonyl isocyanate; Chiral allyl ether; Chiral benzyl ether; 1,4-Amino alcohols; Carbamates;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
Times Cited By Web Of Science : 9  (Related Records In Web of Science)
Times Cited By SCOPUS : 2
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