The Journal of Organic Chemistry

Reductive and Nonreductive Aromatization of Quinol Ketal Glycals. Models for the Preparation of C-Aryl Glycoside Natural Products

KA Parker, CA Coburn, Y Koh

Index: Parker, Kathlyn A.; Coburn, Craig A.; Koh, Yung-hyo Journal of Organic Chemistry, 1995 , vol. 60, # 9 p. 2938 - 2941

Full Text: HTML

Citation Number: 30

Abstract

In the product mixtures from experiments in which the molar ratio of borane to substrate was at least 2: l (Table 2), a significant amount of material was found in a low Rf chromatography fraction (last column). One component of this fraction was isolated and identified as tetrahydropyran 12, presumably the result of overreduction of enol ether 8. The reduction of enol ethers to ethers by excess boraneg is the subject of further study in our labs.

~87%

~84%

~91%

~82%

Suzuki–Miyaura cross-coupling of lithium n-alkylborates

[Zou, Gang; Falck Tetrahedron Letters, 2001 , vol. 42, # 34 p. 5817 - 5819]

Direct catalytic cross-coupling of organolithium compounds

[Giannerini, Massimo; Fananas-Mastral, Martin; Feringa, Ben L. Nature Chemistry, 2013 , vol. 5, # 8 p. 667 - 672]

Functional Group Tolerant Kumada− Corriu− Tamao Coupling of ...

[Vechorkin, Oleg; Proust, Valerie; Hu, Xile Journal of the American Chemical Society, 2009 , vol. 131, # 28 p. 9756 - 9766]

One-step cross-coupling reaction of functionalized alkyl iod...

[Kurono, Nobuhito; Sugita, Kazuya; Takasugi, Shingo; Tokuda, Masao Tetrahedron, 1999 , vol. 55, # 19 p. 6097 - 6108]