Issue 34, 2022
From the journal:

Organic & Biomolecular Chemistry

pH-controlled regioselective nucleophilic ring-opening of epoxide: an improved process for the preparation of (R)-(−)- or (S)-(+)-3-hydroxytetrahydrofuran†

Ankita Chakraborty, ORCID logo ‡ab   Avula Shiva Krishna, ORCID logo ‡ab   Gurrala Sheelu,a   Subhash Ghoshab  and  Thenkrishnan Kumaraguru ORCID logo *ab  

* Corresponding authors

a Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India
E-mail: kumaraguru@iict.res.in

b Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India

Abstract

An environmentally benign, cost-effective and scalable process for the preparation of both the enantiomers of 3-hydroxytetrahydrofuran has been developed. pH-Controlled ring opening of enantiomerically pure epichlorohydrins with cyanohydrin is the key step of the process. The entire protocol does not require any column purification.

Graphical abstract: pH-controlled regioselective nucleophilic ring-opening of epoxide: an improved process for the preparation of (R)-(−)- or (S)-(+)-3-hydroxytetrahydrofuran

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Article information

DOI
https://doi.org/10.1039/D2OB01314B
Article type
Paper
Submitted
21 Jul 2022
Accepted
05 Aug 2022
First published
08 Aug 2022

Org. Biomol. Chem., 2022,20, 6863-6868

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pH-controlled regioselective nucleophilic ring-opening of epoxide: an improved process for the preparation of (R)-(−)- or (S)-(+)-3-hydroxytetrahydrofuran

A. Chakraborty, A. Shiva Krishna, G. Sheelu, S. Ghosh and T. Kumaraguru, Org. Biomol. Chem., 2022, 20, 6863 DOI: 10.1039/D2OB01314B

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