Download PDF
Synfacts 2024; 20(09): 0955
DOI: 10.1055/s-0043-1775006
Metals in Synthesis

Synthesis of anti-1,3-Diols: The Evans–Tishchenko Reaction

Contributor(s):
Mark Lautens
,
Colton E. Johnson
Evans DA, *, Hoveyda AH. Harvard University, Cambridge, USA
Samarium-Catalyzed Intramolecular Tishchenko Reduction of β-Hydroxy Ketones. A Stereoselective Approach to the Synthesis of Differentiated anti 1,3-Diol Monoesters.

J. Am. Chem. Soc. 1990;
112: 6447-6449
DOI: 10.1021/ja00173a071
CrossrefSearch in Google Scholar
› Further Information
 
 PDF Download Permissions and Reprints

Key words

reduction - stereoselective synthesis - 1,3-diols - Evans–Tishchenko reaction

Significance

1,3-Diols are ubiquitous in natural products and bioactive compounds. In 1990, the Evans group reported a highly diastereoselective reduction of β-hydroxy ketones to access anti-1,3-diol monoesters. Importantly, this transformation exhibits wide functional group tolerance and operates under very mild conditions. This has led to its widespread adoption in total syntheses (see Review below).


#

Review

K. J. Ralston, A. N. Hulme Synthesis 2012, 44, 2310–2342.


#

Comment

In the Fürstner synthesis of the formosalides they utilized the Evans–Tishchenko reaction to set a crucial anti-1,3-diol. Interestingly, they also observed an acyl transfer in low yield; this transfer was also found when using this reaction on epimeric starting materials to probe the stereochemistry of the formosalides.


#
#

Publication History

Article published online:
16 August 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany


   Permissions and Reprints