Unprecedented migration of N-alkoxycarbonyl groups in protected pyroglutaminol

Lennart Bunch, Per-Ola Norrby, Karla Frydenvang, Povl Krogsgaard-Larsen, Ulf Madsen

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

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.
Original languageEnglish
JournalORGANIC LETTERS
Volume3
Issue number3
Pages (from-to)433-435
ISSN1523-7060
Publication statusPublished - 2001

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