Investigations of a Nucleophilic Alaninol Synthon Derived from Serine

详细信息    查看全文

• 作者：Mukund P. Sibi ; Drew Rutherford ; Paul A. Renhowe ; and Biqin Li
• 刊名：Journal of the American Chemical Society
• 出版年：1999
• 出版时间：August 25, 1999
• 年：1999
• 卷：121
• 期：33
• 页码：7509 - 7516
• 全文大小：256K
• 年卷期：v.121,no.33(August 25, 1999)
• ISSN：1520-5126

文摘

A nucleophilic synthon, (S)-(+)-4-(2-oxazolidonyl)-methyltriphenylphosphinyl iodide 6, availablefrom L-serine in five steps (overall yield of 52%), reacts with aldehydes to produce alkenes in good to excellentyields (74-89%) and, in some cases, provides excellent stereocontrol of the new double bond. The geometryof the newly formed double bond is influenced by the nature of the aldehyde and reaction conditions. Thetrends in olefin configuration are discussed. Application of this methodology allows for easy preparation ofmolecules containing double bonds allylic to nitrogen, including oxazolidinones and ,-unsaturated aminoalcohols. Several of the unsaturated oxazolidinones are converted to ,-unsaturated amino alcohols in highyields (75 to 90%).