Highly enantioselective synthesis of isoquinuclidine by diels-alder reaction of 1,2-dihydropyridine utilizing chiral bisoxazoline-Cu(II) complex

N. D.M.Romauli Hutabarat, Chigusa Seki, Takashi Shimizu, Masafumi Hirama, Yoshihito Kohari, Hiroto Nakano, Koji Uwai, Nobuhiro Takano, Eunsang Kwon, Haruo Matsuyama

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

The enantioselective Diels-Alder (D-A) reaction between N-phenoxycarbonyl- or N-benzyloxycarbonyl-1,2-dihydropyridine (1a or 1b) and N(2)-acryloyl-N(1)-(1- naphthylmethyl)-5,5-dimethylpyrazolidin-3-one (2b) using (S,S)-bisoxazoline- Cu(II) catalyst (A, B, C or D) has been investigated. Utilizing (S,S)-t-Bu-bisoxazoline-Cu(II) catalyst C, the D-A reaction of 1a and 2 afforded the endo-(7S)-isoquinuclidines (3, 4 or 5) in good chemical yields with high enantioselectivity (up to 99% e.e.).

Original languageEnglish
Pages (from-to)203-217
Number of pages15
JournalHeterocycles
Volume86
Issue number1
DOIs
Publication statusPublished - 2012 Dec 1

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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