Asymmetric Diels–Alder Reaction of α-Substituted and β,β-Disubstituted α,β-Enals via Diarylprolinol Silyl Ether for the Construction of All-Carbon Quaternary Stereocenters

Yujiro Hayashi, Bojan P. Bondzic, Tatsuya Yamazaki, Yogesh Gupta, Shin Ogasawara, Tohru Taniguchi, Kenji Monde

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

The asymmetric Diels–Alder reaction of α-substituted acrolein proceeds in the presence of the trifluoroacetic acid salt of trifluoromethyl-substituted diarylprolinol silyl ether to afford the exo-isomer with both excellent diastereoselectivity and high enantioselectivity. In the Diels–Alder reaction of a β,β-disubstituted α,β-unsaturated aldehyde, good exo-selectivity and excellent enantioselectivity was obtained when the perchloric acid salt of the bulky triisopropyl silyl ether of trifluoromethyl substituted diarylprolinol was employed as an organocatalyst in the presence of water. In both cases, all-carbon quaternary stereocenters are constructed enantioselectively.

Original languageEnglish
Pages (from-to)15874-15880
Number of pages7
JournalChemistry - A European Journal
Volume22
Issue number44
DOIs
Publication statusPublished - 2016 Oct 24

Keywords

  • Diels–Alder reaction
  • all-carbon quaternary stereocenter
  • asymmetric reaction
  • chirality
  • organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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