Direct mono-N-methylation of solid-supported amino acids:: A useful application of the Matteson rearrangement of α-aminoalkylboronic esters

被引：26

作者：

Laplante, C ^{[1
]}

Hall, DG ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 10期

关键词：

D O I：

10.1021/ol015803l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel solid-phase method for the mono-N-methylation of resin supported amino acids was developed on the basis of Matteson's 1,2-carbon to-nitrogen migration of boron in alpha -aminoalkylboronic esters, Amino acids supported on either Wang resin or the highly acid-sensitive SASRIN resin can be methylated by reaction with pinacol chloromethylboronic ester, followed by rearrangement of the resulting aminomethylboronate and subsequent cleavage of the boronate group. This direct method requires only a simple and expedient oxidative resin wash to repair overalkylated sites.

引用

页码：1487 / 1490

页数：4

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