Diastereoselective synthesis of unsaturated 1,2-amino alcohols from α-hydroxy allyl ethers using chlorosulfonyl isocyanate |
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Authors: | Ji Duck Kim |
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Affiliation: | College of Pharmacy, Sungkyunkwan University, Suwon 440-746, South Korea |
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Abstract: | Diastereoselective synthesis of 1,2-amino alcohols was achieved from a highly diastereoselective allylic amination reaction of α-hydroxy allyl ethers using chlorosulfonyl isocyanate. Diastereoselectivities varied depending on the stereochemistry of the ethers used and the stability of the carbocation intermediate obtained during the reaction. We propose that this CSI reaction is the results of either a SNi or SN1 mechanism, according to the stability of the carbocation intermediate. |
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Keywords: | 1,2-Amino alchohols Diastereoselective allylic amination Chlorosulfonyl isocyanate |
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