Synthesis of a chiral quaternary carbon center bearing a fluorine atom: Enantio- and diastereoselective guanidine-catalyzed addition of fluorocarbon nucleophiles

Zhiyong Jiang, Yuanhang Pan, Yujun Zhao, Ting Ma, Richmond Lee, Yuanyong Yang, Kuo-Wei Huang, Ming Wah Wong, Choon Hong Tan

Research output: Contribution to journalArticlepeer-review

128 Scopus citations

Abstract

The perfect combination: The title reaction provides adducts having quaternary carbon centers bearing a fluorine atom with high ee and d.r. values (see scheme). The mechanism and origin of stereoselectivity were elucidated by DFT calculations. The bifunctional mode of the guanidine catalysis was demonstrated in the transition states resulting from the DFT results.

Original languageEnglish (US)
Pages (from-to)3627-3631
Number of pages5
JournalAngewandte Chemie - International Edition
Volume48
Issue number20
DOIs
StatePublished - May 4 2009

Keywords

  • Asymmetric catalysis
  • Fluorine
  • Guanidine
  • Michael addition
  • Transition states

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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