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Asymmetric dithioacetals II: A novel and versatile method for the preparation of chiral dithioacetals

Publication ,  Journal Article
Thérien, M; Gauthier, JY; Young, RN
Published in: Tetrahedron Letters
January 1, 1988

Reaction of aldehydes with one equivalent each of a thiol and a chiral thiolacid such as (R)-(-)-α-methoxyphenylthiolacetic acid in the presence of an acidic catalyst such as ZnI2 or p-toluenesulfonic acid yields diastereomeric mixed thioacetals in good yields which are generally readily separable. Subsequent deacylation at low temperature with sodium methoxide and alkylation of the resulting thiolate anion with a variety of electrophiles provides chiral dithioacetals with no loss of enantiomeric purity. © 1988.

Duke Scholars

Published In

Tetrahedron Letters

DOI

ISSN

0040-4039

Publication Date

January 1, 1988

Volume

29

Issue

51

Start / End Page

6733 / 6736

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 3101 Biochemistry and cell biology
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry
 

Citation

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ICMJE
MLA
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Thérien, M., Gauthier, J. Y., & Young, R. N. (1988). Asymmetric dithioacetals II: A novel and versatile method for the preparation of chiral dithioacetals. Tetrahedron Letters, 29(51), 6733–6736. https://doi.org/10.1016/S0040-4039(00)82441-7
Thérien, M., J. Y. Gauthier, and R. N. Young. “Asymmetric dithioacetals II: A novel and versatile method for the preparation of chiral dithioacetals.” Tetrahedron Letters 29, no. 51 (January 1, 1988): 6733–36. https://doi.org/10.1016/S0040-4039(00)82441-7.
Thérien M, Gauthier JY, Young RN. Asymmetric dithioacetals II: A novel and versatile method for the preparation of chiral dithioacetals. Tetrahedron Letters. 1988 Jan 1;29(51):6733–6.
Thérien, M., et al. “Asymmetric dithioacetals II: A novel and versatile method for the preparation of chiral dithioacetals.” Tetrahedron Letters, vol. 29, no. 51, Jan. 1988, pp. 6733–36. Scopus, doi:10.1016/S0040-4039(00)82441-7.
Thérien M, Gauthier JY, Young RN. Asymmetric dithioacetals II: A novel and versatile method for the preparation of chiral dithioacetals. Tetrahedron Letters. 1988 Jan 1;29(51):6733–6736.
Journal cover image

Published In

Tetrahedron Letters

DOI

ISSN

0040-4039

Publication Date

January 1, 1988

Volume

29

Issue

51

Start / End Page

6733 / 6736

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 3101 Biochemistry and cell biology
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry