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 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.
Jung
Young Hoon
YH
Organic & Medicinal Chemistry Laboratory, College of Pharmacy, Sungkyunkwan University, Suwon 440-746, Korea. yhjung@skku.ac.kr
Kim
Ji Duck
JD
D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002219:Carbamates / Q000737:chemistry; D004987:Ethers / Q000737:chemistry; D017953:Isocyanates / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000605:Amino Alcohols; D002219:Carbamates; D004987:Ethers; D017953:Isocyanates; C487390:chlorosulfonyl isocyanate