A practical strategy for the structural diversification of aliphatic scaffolds through the palladium-catalyzed picolinamide-directed remote functionalization of unactivated C(sp3)-H bonds

Gang He, Gong Chen

Research output: Contribution to journalArticle

263 Citations (Scopus)

Abstract

Hats off to the director: High levels of regio- and stereoselectivity were observed for a broad range of amine substrates with aryl and vinyl iodide coupling partners in the title reaction. The synthetic utility of this strategy was highlighted by the ready preparation from threonine of 1, with a removable picolinamide auxiliary PAr, and its coupling with 2 in a concise formal synthesis of (+)-obafluorin. TBS=tert-butyldimethylsilyl.

Original languageEnglish (US)
Pages (from-to)5192-5196
Number of pages5
JournalAngewandte Chemie - International Edition
Volume50
Issue number22
DOIs
StatePublished - May 23 2011

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Stereoselectivity
Regioselectivity
Palladium
Threonine
Scaffolds
Amines
Substrates
picolinamide
vinyl iodide
obafluorin

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

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