Unprecedented migration of N-alkoxycarbonyl groups in protected pyroglutaminol

被引：20

作者：

Bunch, L ^{[1
]}

Norrby, PO ^{[1
]}

Frydenvang, K ^{[1
]}

Krogsgaard-Larsen, P ^{[1
]}

Madsen, U ^{[1
]}

机构：

[1] Royal Danish Sch Pharm, Dept Med Chem, Ctr Drug Design & Transport, DK-2100 Copenhagen, Denmark

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 03期

关键词：

D O I：

10.1021/ol0069397

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Cleavage of an O-silyl ether in an NBOC protected pyroglutaminol using TBAF led to an unprecedented migration of the BOC group. An investigation of the mechanism, based on experimental data and quantum mechanical calculations, is presented. Similar migration was observed for KCbz and N-methoxycarbonyl groups.

引用

页码：433 / 435

页数：3

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