|Publication Type||Journal Article|
|Year of Publication||2006|
|Authors||Ng, PYee, Masse, CE, Shaw, JT|
|Date Published||2006 Aug 31|
|Keywords||Anhydrides, Imines, Models, Molecular, Molecular Structure, Pyrroles, Quinolines|
Arylthio-substituted succinic anhydrides undergo cycloaddition reactions with imines to produce gamma-lactams in high yield and with high diastereoselectivity. The origin of the selectivity is proposed to result from anion-pi repulsion in the transition state. The utility of this technique is demonstrated in a synthesis of the carbon framework common to the alkaloids martinellic acid and martinelline in five steps.
|Alternate Journal||Org. Lett.|