Oranocatalytic Asymmetric Michael Addition For The Synthesis Of Chiral Indolin-3-one Derivatives

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.