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

Fingerprint

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.
@article{94f2e144e6b444aa9ce4a416e5c6346b,
title = "Kinetic resolution of phosphoryl and sulfonyl esters of 1,1′-bi-2-naphthol via Pd-catalyzed alcoholysis of their vinyl ethers",
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.",
author = "Takeshi Sakuma and Eiji Yamamoto and Hiroshi Aoyama and Yasushi Obora and Yasushi Tsuji and Makoto Tokunaga",
year = "2008",
month = "7",
day = "11",
doi = "10.1016/j.tetasy.2008.06.034",
language = "English",
volume = "19",
pages = "1593--1599",
journal = "Tetrahedron Asymmetry",
issn = "0957-4166",
publisher = "Elsevier Limited",
number = "13",

}

TY - JOUR

T1 - Kinetic resolution of phosphoryl and sulfonyl esters of 1,1′-bi-2-naphthol via Pd-catalyzed alcoholysis of their vinyl ethers

AU - Sakuma, Takeshi

AU - Yamamoto, Eiji

AU - Aoyama, Hiroshi

AU - Obora, Yasushi

AU - Tsuji, Yasushi

AU - Tokunaga, Makoto

PY - 2008/7/11

Y1 - 2008/7/11

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=48949114897&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=48949114897&partnerID=8YFLogxK

U2 - 10.1016/j.tetasy.2008.06.034

DO - 10.1016/j.tetasy.2008.06.034

M3 - Article

VL - 19

SP - 1593

EP - 1599

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

SN - 0957-4166

IS - 13

ER -

Access to Document