Journal of the Chemical Society. Perkin Transactions 1 (2001) p. 1977 - 1982 (2000)
Update date:2022-08-04
Topics: Diastereoselectivity Yield NMR spectroscopy Enantiomeric excess alkylations Bicyclic Lactams Experimental terms Chiral chromatography
Bailey, Jonathan H.
Byfield, Andrew T.J.
Davis, Philip J.
Foster, Alison C.
Leech, Michael
Moloney, Mark G.
Mueller, Matthias
Keith Prout
The diastereoselectivity in the alkylation of the enolates of bicyclic lactams 2 derived from pyroglutaminol la has been found to depend upon the nature of the hemiaminal ether protecting group. Although exo-alkylation has been widely reported for 2a,b,e, endo-alkylation is favoured for 2d. It is postulated that this is a result of the opening of the bicyclic structure of the enolate derived from 2d, and the consequent stereoelectronic facilitation of endo-facial attack.
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