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Preparation of the P(NMeOMe)3 and It’s Application in Synthesis of Weinreb Amides

Author: NiuTeng
Tutor: HuYuLai
School: Northwest Normal University
Course: Organic Chemistry
Keywords: Weinreb amides acylating microwave solvent-free
CLC: O631.3
Type: Master's thesis
Year: 2008
Downloads: 2
Quote: 0
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Abstract


Weinreb amides (N-Methoxy-N-methyl amides) have become very important and effective acylating agents since its original discovery by Nahm and Weinreb in 1981. They can cleanly react with Grignard reagentsand and organolithium to give ketones even with excess of organometallc reagents. Because of their effectiveness as acylating reagents they have been used in synthesis of some natural products. Significant effort has been devoted toward the development of mild and general methods for their synthesis in recent years. Of all the methods the direct conversion of carboxylic acid to the corresponding Weinreb amides is a very attractive. Peptide coupling reagents are used in literature. It is one of the major important and more challenges to direct conversion of carboxylic acid to the corresponding Weinreb amides iorganic chemistry. Based on this point of view, a powerful reagent for synthesis of Weinreb amides is directly from carboxylic acid. Allowing for the recent development of the green chemistry, our research group set out from the green-friendly point, the synthesis of Weinreb amides was first touch upon under the condition of microwave and solvent-freeness. The following three parts are mainly included.1. In the first chapter, the product, development, preparation and application in organic synthesis of Weinreb amides, are reviewed in detail.2. In Chapter 2, the preparation of P(NOMeMe)3 reagent was mainly studied, and the reagent was used in the synthesis of Weinreb amides for the first time. It can produce Weinreb amide efficiency by carboxylic acid in one step, and the configuration of Weinreb amide will be unchanged. This will provide some theoretical bases of useful synthon for structural diversity of total synthesis of natural product.3. In Chapter 3, microwave and non-solvent technique was introduced in the synthesis of Weinreb amides. The influence of microwave radiation on the Weinreb amides was investigated. In this experiment, carboxylic acid reacts with P(NOMeMe)3 in 10 minutes, under the condition of non-solvent and microwave illumination. It provides a simple and fast method of synthesis of environment-friendship.

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