911291-90-2Relevant academic research and scientific papers
Cycloaddition reactions of imines with 3-thiosuccinic anhydrides: Synthesis of the tricyclic core of martinellic acid
Ng, Pui Yee,Masse, Craig E.,Shaw, Jared T.
, p. 3999 - 4002 (2006)
Arylthio-substituted succinic anhydrides undergo cycloaddition reactions with imines to produce γ-lactams in high yield and with high diastereoselectivity. The origin of the selectivity is proposed to result from anion-π 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.
