Alkylation reactions using alpha- halolactams or lactam enolates derived from bicyclic lactam templates can proceed with high endo- or exo- diastereoselectivity respectively. In the latter case, stereochemical correction by means of enolate generation and hindered phenol quench is possible with moderate efficiency. This protocol has been applied to the synthesis of protected penmacric acid and its analogues.
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Univ So Mississippi, Sch Polymers & High Performance Mat, Hattiesburg, MS 39406 USAUniv So Mississippi, Sch Polymers & High Performance Mat, Hattiesburg, MS 39406 USA
Parrish, DA
Mathias, LJ
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Univ So Mississippi, Sch Polymers & High Performance Mat, Hattiesburg, MS 39406 USAUniv So Mississippi, Sch Polymers & High Performance Mat, Hattiesburg, MS 39406 USA
Mathias, LJ
Moore, KM
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Univ So Mississippi, Sch Polymers & High Performance Mat, Hattiesburg, MS 39406 USAUniv So Mississippi, Sch Polymers & High Performance Mat, Hattiesburg, MS 39406 USA