Synthesis of ;2;²-homophenylalanine derivatives by Negishi cross-coupling reactions

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• 作者：Hannah E. Bartrum ; Harry Adams ; Lorenzo Caggiano ; Richard F.W. Jackson
• 关键词：Malmquist productivity ; Electricity ; Efficiency
• 刊名：Tetrahedron
• 出版年：2008
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：21 April 2008
• 卷：64
• 期：17
• 页码：3701-3712
• 文件大小：588 K

摘要

Three approaches to the synthesis of ;2;²-homophenylalanine derivatives using Negishi cross-coupling reaction are reported. In the first two approaches, two protected 204e.gif" alt="greek small letter alpha" title="greek small letter alpha" border="0">-iodomethyl-;2;-amino esters are each converted into the corresponding organozinc iodides, which then undergo Pd-catalysed cross-coupling with aromatic halides to give ;2;²-homophenylalanine derivatives, and the X-ray crystal structure of one product is reported. Alternatively, Negishi cross-coupling of the zinc reagent derived from N-benzyl 3-iodomethyl azetidin-2-one and aryl halides gave 3-benzylazetidin-2-ones, masked ;2;²-homophenylalanine derivatives. The X-ray crystal structure of 1-benzyl-3-[(p-toluenesulfonyloxy)-methyl]-azetidin-2-one confirms the structural assignment.