PDF(Pubmed)
Abstract：
This paper describes the three-step synthesis of TBS-MAC, a masked acyl cyanide (MAC) and a versatile one-carbon oxidation state three synthon. We have developed a scalable and detailed synthesis that involves: (1) acetylation of malononitrile to form the sodium enolate, (2) protonation of the enolate to form acetylmalononitrile, and (3) epoxidation of the enol, rearrangement to an unstable alcohol, and TBS-protection to form the title compound. Both the sodium enolate and acetylmalononitrile are bench-stable precursors to the intermediate hydroxymalononitrile, which can be converted to other MAC reagents beyond TBS by varying the protecting group (Ac, MOM, EE, etc.).
摘要：
本文介绍了TBS-MAC的三步合成，掩蔽的酰基氰化物（MAC）和通用的一碳氧化态三合成子。我们已经开发了一种可扩展的详细合成方法，包括：（1）丙二腈乙酰化形成烯醇钠，(2)烯醇化物质子化形成乙酰丙二腈，和（3）烯醇的环氧化，重新排列成不稳定的酒精，和TBS保护以形成标题化合物。烯醇钠和乙酰丙二腈都是中间体羟基丙二腈的实验室稳定前体，通过改变保护基团(Ac，妈妈,EE,等。).
