Abstract
In this thesis, a new carbon-carbon bond formation via zinc-ammonia mediated intermolecular carbonyl-ene reductive coupling reaction was studied. We have developed a novel methodology to provide 3,3-disubstituted phthalide derivatives in good to excellent yield under ambient conditions. In this reaction, the various types of alkenes, including acrylonitrile, acrylate, acrylamide, vinyl sulfoxide and even sterically hindered olefin successfully participated, and the desired product was obtained in good to excellent yield. Similarly, different types of 2-substituted methyl benzoate were also tolerated well to give the corresponding phthalide derivatives in good yield in one-pot operation. This reaction provides a powerful method for the synthesis of highly functionalized phthalide derivatives which can be applied to the synthesis of various natural products and be also useful for other functional group transformation reaction.