An alkoxide anion-triggered tert-butyloxycarbonyl group migration. Mechanism and application

Fengtian Xue, Richard B. Silverman*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

We report a fast N→O tert-butyloxycarbonyl (Boc) migration of the imide (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-hyd roxypyrrolidine-1-carboxylate (2) via a base-generated alkoxide. The mechanism of the migration is intramolecular, involving an unusual nine-membered cyclic transition state.

Original languageEnglish (US)
Pages (from-to)2536-2538
Number of pages3
JournalTetrahedron Letters
Volume51
Issue number18
DOIs
StatePublished - May 5 2010

Keywords

  • Boc group migration
  • Cross-over experiment
  • Intramolecular migration
  • N to O migration

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'An alkoxide anion-triggered tert-butyloxycarbonyl group migration. Mechanism and application'. Together they form a unique fingerprint.

Cite this