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The Pyranoside Ring as a Nucleophile in Aldol Condensations

Publication ,  Journal Article
Handa, S; Tsang, R; Mcphail, AT; Fraser-reid, B
Published in: Journal of Organic Chemistry
July 1, 1987

The enolate derived from a 2-deoxy-3-keto-hexopyranoside undergoes aldol condensations in high yields. With respect to the newly formed bond, the orientation at C2 is always axial, indicating that the pyranoside moiety exerts excellent stereoselectivity at that center. Although the enolate appears to induce little facial selectivity in the aldehyde partner, a-substituents in the latter have a profound effect, the product being formed according to the Felkin-Anh model. Thus, the acetonides of Rand Sglyceraldehydes react to give syn and anti products, respectively, with complete stereoselectivity in each case. © 1987, American Chemical Society. All rights reserved.

Duke Scholars

Published In

Journal of Organic Chemistry

DOI

EISSN

1520-6904

ISSN

0022-3263

Publication Date

July 1, 1987

Volume

52

Issue

15

Start / End Page

3489 / 3491

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry
 

Citation

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MLA
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Handa, S., Tsang, R., Mcphail, A. T., & Fraser-reid, B. (1987). The Pyranoside Ring as a Nucleophile in Aldol Condensations. Journal of Organic Chemistry, 52(15), 3489–3491. https://doi.org/10.1021/jo00391a074
Handa, S., R. Tsang, A. T. Mcphail, and B. Fraser-reid. “The Pyranoside Ring as a Nucleophile in Aldol Condensations.” Journal of Organic Chemistry 52, no. 15 (July 1, 1987): 3489–91. https://doi.org/10.1021/jo00391a074.
Handa S, Tsang R, Mcphail AT, Fraser-reid B. The Pyranoside Ring as a Nucleophile in Aldol Condensations. Journal of Organic Chemistry. 1987 Jul 1;52(15):3489–91.
Handa, S., et al. “The Pyranoside Ring as a Nucleophile in Aldol Condensations.” Journal of Organic Chemistry, vol. 52, no. 15, July 1987, pp. 3489–91. Scopus, doi:10.1021/jo00391a074.
Handa S, Tsang R, Mcphail AT, Fraser-reid B. The Pyranoside Ring as a Nucleophile in Aldol Condensations. Journal of Organic Chemistry. 1987 Jul 1;52(15):3489–3491.
Journal cover image

Published In

Journal of Organic Chemistry

DOI

EISSN

1520-6904

ISSN

0022-3263

Publication Date

July 1, 1987

Volume

52

Issue

15

Start / End Page

3489 / 3491

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry