External chiral ligand-induced enantioselective lithiation/S(E)2 reactions of isochroman and phthalan

Katsuhiko Tomooka, L. F. Wang, F. Okazaki, T. Nakai

Research output: Contribution to journalArticle

49 Citations (Scopus)

Abstract

Treatment of isochroman and phthalan with a t-BuLi/chiral bis(oxazoline) complex followed by reaction with carbon-electrophiles such as benzaldehyde and CO2 is shown to afford the α-substituted derivatives in moderate-to-high enantioselectivities (up to 97% ee and 83% ee, respectively). The asymmetric induction is proved to occur at the post-lithiation step. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)6121-6125
Number of pages5
JournalTetrahedron Letters
Volume41
Issue number32
DOIs
Publication statusPublished - Aug 5 2000
Externally publishedYes

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Enantioselectivity
Carbon
Ligands
Derivatives
folpet
benzaldehyde

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

External chiral ligand-induced enantioselective lithiation/S(E)2 reactions of isochroman and phthalan. / Tomooka, Katsuhiko; Wang, L. F.; Okazaki, F.; Nakai, T.

In: Tetrahedron Letters, Vol. 41, No. 32, 05.08.2000, p. 6121-6125.

Research output: Contribution to journalArticle

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