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Koenigs-Knorr reaction selectivity

PROBLEM 22.20 The Koenigs-Knorr reaction is useful for making glycosides. In this reaction, the pentaacetate compound of Figure 22.37 is treated with HBr to give the C(l) bromide.The bromide is then replaced by an alcohol in the presence of AgaO.The reaction is very selective for the P anomer, but a series of experiments has established that it is not a simple Sn2 reaction. Show a mechanism that explains the selective formation of the P anomer. Hint Remember Chapter 21. [Pg.1149]

Therefore, the interest in studying this reaction lies in its sensitivity to the microenvironment and ion complexation. As Ag" cation forms strong complex with the diaza 18 crown 6 we expected a selectivity modification by carrying out the Koenigs-Knorr reaction in the presence of the immobilized ligand. [Pg.410]

See other pages where Koenigs-Knorr reaction selectivity is mentioned: [Pg.161]    [Pg.89]    [Pg.51]    [Pg.212]    [Pg.112]    [Pg.93]    [Pg.161]    [Pg.64]    [Pg.626]    [Pg.60]    [Pg.28]    [Pg.112]    [Pg.22]    [Pg.286]    [Pg.139]    [Pg.335]    [Pg.34]    [Pg.97]    [Pg.150]    [Pg.46]    [Pg.47]    [Pg.167]    [Pg.161]    [Pg.150]    [Pg.27]    [Pg.180]    [Pg.304]    [Pg.155]    [Pg.193]    [Pg.46]    [Pg.47]    [Pg.155]    [Pg.400]    [Pg.38]    [Pg.95]    [Pg.198]   
See also in sourсe #XX -- [ Pg.34 , Pg.85 ]

See also in sourсe #XX -- [ Pg.85 ]



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