Enantioselective reactions of α-methoxybenzyllithium generated by t-BuLi/chiral bis(oxazoline) complex with aldehydes

Katsuhiko Tomooka, Lan Fang Wang, Nobuyuki Komine, Takeshi Nakai

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

The title reaction is shown to afford the corresponding 1,2-diol monomethyl ethers in moderate-to-high levels of % ee (up to 98%) and % de (up to 90% anti), depending markedly on the aldehyde reactivity. The origin of the enantioselectivity is discussed in terms of a dynamic thermodynamic resolution mechanism.

Original languageEnglish
Pages (from-to)6813-6816
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number37
DOIs
Publication statusPublished - Sep 10 1999

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Ethers
Enantioselectivity
Thermodynamics
Aldehydes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Enantioselective reactions of α-methoxybenzyllithium generated by t-BuLi/chiral bis(oxazoline) complex with aldehydes. / Tomooka, Katsuhiko; Wang, Lan Fang; Komine, Nobuyuki; Nakai, Takeshi.

In: Tetrahedron Letters, Vol. 40, No. 37, 10.09.1999, p. 6813-6816.

Research output: Contribution to journalArticle

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