An improved method for the protection of carboxylic acids as 1,1-dimethylallyl esters.
An improved method for the protection of carboxylic acids as 1,1-dimethylallyl esters.
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一种将羧酸保护为 1,1-二甲基烯丙酯的改进方法。
DOI：
10.1021/jo061207z
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发表时间：
2006
期刊：
影响因子：
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通讯作者：
Lipton,MarkA
中科院分区：
文献类型：
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作者：
Sedighi,Minoo;Calimsiz,Selçuk;Lipton,MarkA
各种N-保护的氨基酸的1，1-二甲基烯丙基（DMA）酯已经使用异戊二烯基二甲基锍四氟硼酸盐（一种可以容易地制备和储存的试剂）结合催化剂CuBr合成。这些反应在几小时内完成，并以高产率得到DMA酯。正如我们小组先前所示，DMA酯代表了羧酸的钯不稳定保护基团，其与叔丁基酯一样抵抗亲核攻击。
1,1-Dimethylallyl (DMA) esters of various N-protected amino acids have been synthesized using prenyldimethylsulfonium tetrafluroborate, a reagent that can be readily made and stored, in conjunction with catalytic CuBr. These reactions were complete within several hours and afforded DMA esters in high yields. As has been previously shown in our group, DMA esters represent a palladium-labile proctecting group for carboxylic acids that resists nucleophilic attack as atert-butyl ester would.