Issue 5, 2015

Et3B-mediated two- and three-component coupling reactions via radical decarbonylation of α-alkoxyacyl tellurides: single-step construction of densely oxygenated carboskeletons

Abstract

The single-step construction of various densely oxygenated carboskeletons was achieved by radical-based two- and three-component coupling reactions of sugar derivatives, without the need for light or heat. Et3B/O2-mediated decarbonylation readily converted α-alkoxyacyl tellurides to α-alkoxy carbon radicals, which intermolecularly added to glyoxylic oxime ether or enones to provide the two-component adducts. Furthermore, the three-component adducts were produced by an intermolecular aldol reaction between the aldehyde and the boron enolates generated by capture of the two-component radical intermediates by Et3B. This powerful coupling method serves as a novel strategy for the convergent synthesis of polyol natural products.

Graphical abstract: Et3B-mediated two- and three-component coupling reactions via radical decarbonylation of α-alkoxyacyl tellurides: single-step construction of densely oxygenated carboskeletons

Supplementary files

Article information

Article type
Edge Article
Submitted
06 Feb 2015
Accepted
05 Mar 2015
First published
06 Mar 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2015,6, 2765-2769

Et3B-mediated two- and three-component coupling reactions via radical decarbonylation of α-alkoxyacyl tellurides: single-step construction of densely oxygenated carboskeletons

M. Nagatomo, D. Kamimura, Y. Matsui, K. Masuda and M. Inoue, Chem. Sci., 2015, 6, 2765 DOI: 10.1039/C5SC00457H

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