On the diastereoselectivity of alkylations of bicyclic lactams

作者: Jonathan H. Bailey , Andrew T. J. Byfield , Philip J. Davis , Alison C. Foster , Michael Leech

DOI: 10.1039/B000432O

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摘要: The diastereoselectivity in the alkylation of enolates bicyclic lactams 2 derived from pyroglutaminol 1a has been found to depend upon nature hemiaminal ether protecting group. Although exo-alkylation widely reported for 2a,b,e, endo-alkylation is favoured 2d. It postulated that this a result opening structure enolate 2d, and consequent stereoelectronic facilitation endo-facial attack.

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