Phosphinamide-Directed Benzylic Lithiation. Application to the Synthesis of Peptide Building Blocks

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• 作者：Pascual O&ntilde ; a Burgos ; Ignacio Ferná ; ndez ; Marí ; a José ; Iglesias ; Santiago Garcí ; a-Granda ; Fernando Ló ; pez Ortiz
• 刊名：Organic Letters
• 出版年：2008
• 出版时间：February 21, 2008
• 年：2008
• 卷：10
• 期：4
• 页码：537 - 540
• 全文大小：102K
• 年卷期：v.10,no.4(February 21, 2008)
• ISSN：1523-7052

文摘

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N-Benzyldiphenylphosphinamides are deprotonated at the NC_{fchars/alpha.gif" BORDER=0>} position diastereospecifically upon treatment with t-BuLi in diethyl ether at lowtemperature. The reaction of the anions with alkyl, acyl, and tin halides, aliphatic and aromatic aldehydes, and Michael acceptors allowedinstallation of a variety of functional groups into the benzylic arm in excellent yields. Cleavage of the P-N linkage affords 1,2-amino alcoholsand fchars/alpha.gif" BORDER=0>-, fchars/beta2.gif" BORDER=0 ALIGN="middle">-, and fchars/gamma.gif" BORDER=0 >-amino acids.