Issue 1, 2016

A highly diastereoselective “super silyl” governed aldol reaction: synthesis of α,β-dioxyaldehydes and 1,2,3-triols

Abstract

A highly diastereoselective approach for the synthesis of protected α,β-dioxyaldehydes derived from (Z)-tris(trimethylsilyl)silyl “super silyl” enol ethers is described. A general and highly syn-stereoselective aldol reaction directed by the “super silyl” group catalyzed by triflimide (HNTf2) is developed providing α,β-dioxyaldehydes and 1,2,3-triol fragments which can be a useful platform for the elaboration of natural and unnatural sugar derivatives.

Graphical abstract: A highly diastereoselective “super silyl” governed aldol reaction: synthesis of α,β-dioxyaldehydes and 1,2,3-triols

Supplementary files

Article information

Article type
Edge Article
Submitted
03 Sep 2015
Accepted
05 Oct 2015
First published
06 Oct 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 license

Chem. Sci., 2016,7, 394-399

Author version available

A highly diastereoselective “super silyl” governed aldol reaction: synthesis of α,β-dioxyaldehydes and 1,2,3-triols

W. Gati and H. Yamamoto, Chem. Sci., 2016, 7, 394 DOI: 10.1039/C5SC03307A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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