【作者】 刘耀宗；

【导师】 许鹏飞；

【作者基本信息】 兰州大学 ， 有机化学， 2012， 博士

【摘要】 本论文主要包括两部分内容：1.对近几年有机催化Michael加成反应的研究进展进行了综述Michael加成反应是有机化学合成反应中构建碳-碳键的重要反应之一,一直是化学工作者感兴趣的研究课题。在过去的几年里,不对称有机催化Michael加成反应得到了迅速发展,成为不对称催化研究领域的一个热点。和其他有机催化反应一样,它具有条件温和、反应时间短、立体选择性好、原料及反应后处理简单等优点。随着各种催化体系的发展和完善,有机催化Michael加成反应已经成为合成众多重要的药物中间体和天然产物手性合成子的有效手段。本章主要总结了有机催化Michael加成反应在近几年的研究进展。2.有机催化不对称Michael加成反应合成手性吲哚-3-酮衍生物的研究吲哚-3-酮衍生物广泛存在于许多天然产物和药物分子中,同时也是很多重要生物活性分子合成的起始原料。我们用简单的乙酰基保护的吲哚-3-酮分别与硝基烯烃,不饱和醛和不饱和酮酯进行加成反应,在相应的有机小分子催化剂的催化下,均以很好的产率和立体选择性合成了手性的2-位取代的吲哚酮类化合物,该产物可以转化为手性的2-位取代吲哚和吲哚啉并环戊烷类化合物。该反应简洁高效,催化效率高,为手性的氧化吲哚及吲哚类化合物的合成提供了一种切实有效的方法。更多还原

【Abstract】 This thesis is composed of two parts:1. The review of asymmetric organocatalytic Michael additionThe Michael addition reaction is one of the most important reactions for the formation of carbon-carbon bonds in organic synthesis, which has attracted considerable interest from chemists all over the world. Remarkable progress has been made in this field in recent years and the research in organocatalytic asymmetric Michael addition has become a big hit in the field of asymmetric catalysis. It has the advantages of mild reaction conditions, short reaction time, excellent stereoselectivities, readily available starting materials with a minimum of manual operations. The organocatalytic asymmetric Michael addition has become effective methods for the synthesis of many important drug intermediates and chiral synthons of natural products. This chapter reviews the recent development of asymmetric organocatalytic Michael addition reaction according to the catalyst system used.2. Organocatalytic asymmetric Michael addition for the synthesis of chiral indolin-3-one derivatives2-Substituted indolin-3-ones exist widely in many natural products and pharmaceutical compounds, and have been used as versatile intermediates for the synthesis of biologically active organic compounds and natural-products. We investigated the reactions of1-acetylindolin-3-ones with nitroolefins, α,β-unsaturated aldehydes and β,γ-unsaturated α-keto esters catalyzed by corresponding organocatalysts,2-substituted indolin-3-ones were obtained in good yields and stereoslectivities, which could be transformed to chiral2-substituted indoles and cyclopentyl[b]indoline compounds. This concise and simple reaction with high catalytic efficiency could be an effective method for the synthesis of chiral3-oxindoles and indole compounds.更多还原