Kinetic resolution of phosphoryl and sulfonyl esters of 1,1′-bi-2-naphthol via Pd-catalyzed alcoholysis of their vinyl ethers

Takeshi Sakuma, Eiji Yamamoto, Hiroshi Aoyama, Yasushi Obora, Yasushi Tsuji, Makoto Tokunaga

Research output: Contribution to journal › Article

11 Citations (Scopus)

Abstract

Kinetic resolution of phosphoryl and sulfonyl esters of 1,1′-bi-2-naphthol has been achieved via the Pd-catalyzed alcoholysis of their vinyl ethers. The highest krel value reached 36.8 with substrate 3c, and (R)-3c 99.0% ee was obtained in 43% isolated yield.

Original languageEnglish
Pages (from-to)1593-1599
Number of pages7
JournalTetrahedron Asymmetry
Volume19
Issue number13
DOIs
Publication statusPublished - Jul 11 2008

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Naphthol
esters
Ethers
ethers
Esters
Kinetics
kinetics
Substrates
2-naphthol
vinyl ether

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Kinetic resolution of phosphoryl and sulfonyl esters of 1,1′-bi-2-naphthol via Pd-catalyzed alcoholysis of their vinyl ethers. / Sakuma, Takeshi; Yamamoto, Eiji; Aoyama, Hiroshi; Obora, Yasushi; Tsuji, Yasushi; Tokunaga, Makoto.

In: Tetrahedron Asymmetry, Vol. 19, No. 13, 11.07.2008, p. 1593-1599.

Research output: Contribution to journal › Article

Sakuma, T, Yamamoto, E, Aoyama, H, Obora, Y, Tsuji, Y & Tokunaga, M 2008, 'Kinetic resolution of phosphoryl and sulfonyl esters of 1,1′-bi-2-naphthol via Pd-catalyzed alcoholysis of their vinyl ethers', Tetrahedron Asymmetry, vol. 19, no. 13, pp. 1593-1599. https://doi.org/10.1016/j.tetasy.2008.06.034
Sakuma T, Yamamoto E, Aoyama H, Obora Y, Tsuji Y, Tokunaga M. Kinetic resolution of phosphoryl and sulfonyl esters of 1,1′-bi-2-naphthol via Pd-catalyzed alcoholysis of their vinyl ethers. Tetrahedron Asymmetry. 2008 Jul 11;19(13):1593-1599. https://doi.org/10.1016/j.tetasy.2008.06.034
Sakuma, Takeshi ; Yamamoto, Eiji ; Aoyama, Hiroshi ; Obora, Yasushi ; Tsuji, Yasushi ; Tokunaga, Makoto. / Kinetic resolution of phosphoryl and sulfonyl esters of 1,1′-bi-2-naphthol via Pd-catalyzed alcoholysis of their vinyl ethers. In: Tetrahedron Asymmetry. 2008 ; Vol. 19, No. 13. pp. 1593-1599.
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