Enantioselective intramolecular AZA-spiroannulation onto benzofurans using chiral rhodium catalysis

Takuro Shibuta, Shigeki Sato, Masatoshi Shibuya, Naoki Kanoh, Tohru Taniguchi, Kenji Monde, Yoshiharu Iwabuchi

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

The development of efficient and enantioselective intramolecular aza-spiroannulation onto benzofurans using chiral rhodium catalysis is described. The optimized reaction conditions [Rh2(S-TCPTAD) 4 (3 mol %), PhIO (1.6 equiv), MeOH (10 equiv) in PhCF3, 0°C] brought about oxidative aza-spiroannulation of 3-(carbamoylmethyl) benzofuran (3) resulting in (2R,3S)-2-methoxy-2H-spiro- [benzofuran-3,4′- oxazolidin]-2′-one (15a) in 69% yield with 86% ee, the absolute structure of which was determined by a combination of X-ray crystallography and vibrational circular dichroism (VCD) spectroscopy. The reaction is applicable to the asymmetric construction of various 2,3-dihydrobenzofuran derivatives bearing a nitrogen-containing tetrasubstituted carbon stereocenter at C3 (up to 92% ee).

Original languageEnglish
Pages (from-to)631-639
Number of pages9
JournalHeterocycles
Volume89
Issue number3
DOIs
Publication statusPublished - 2014

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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