Diastereoselective synthesis of unsaturated 1,4-amino alcohols as a biologically important moiety

The diastereoselective synthesis of unsaturated 1.4-amino alcohols can be achieved using 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...

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Bibliographic Details
Published inArchives of pharmacal research Vol. 28; no. 4; pp. 382 - 390
Main Authors Jung, Young Hoon, Kim, Ji Duck
Format Journal Article
LanguageEnglish
Published Korea (South) 01.04.2005
Subjects
Amino Alcohols - chemical synthesis
Amino Alcohols - chemistry
Carbamates - chemistry
Ethers - chemistry
Isocyanates - chemistry
Molecular Structure
Stereoisomerism
Structure-Activity Relationship
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Summary:The diastereoselective synthesis of unsaturated 1.4-amino alcohols can be achieved using 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 SNi (retention) and a SN1 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.
Bibliography:ObjectType-Article-1
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ISSN:0253-6269
1976-3786
DOI:10.1007/BF02977665