A practical ruthenium-catalyzed cleavage of the allyl protecting group in amides, lactams, imides, and congeners

A practical ruthenium-catalyzed cleavage of the allyl protecting group in amides, lactams, imides, and congeners
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DOI:
10.1002/chem.200501227
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发表时间:
2006-03-20
影响因子:
4.3
通讯作者:
Alonso, JM
Alonso, JM
中科院分区:
化学2区
文献类型:
--
作者:
Alcaide, B;Almendros, P;Alonso, JM

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提出了一种简便的n -烯丙基酰胺类基团脱保护方法。钌催化的酰胺类、内酰胺类、亚胺类、吡唑烷酮类、酰脲类和恶唑烷酮类脱烯化反应的第一个例子是通过依次使用Grubbs卡宾(异构化步骤)和RUCl3(氧化步骤)实现的。可以使用多种底物,包括对映体纯多功能β -内酰胺和γ -内酰胺。
A convenient methodology for the deprotection of N-allylic amide-like moieties was developed. The first examples accounting for the ruthenium-catalyzed deallylation of amides, lactams, imides, pyrazolidones, hydantoins, and oxazolidinones have been achieved by the sequential use of Grubbs carbene (isomerization step) and RUCl3 (oxidation step). A variety of substrates, including enantio-pure multifunctional beta- and gamma-lactams, can be employed.