The Synthetic Approaches to 1,2-Chlorohydrins

Abstract

This short review highlights the hitherto realised synthetic approaches towards organic 1,2-chlorohydrins by functionalisation of alkenes (i.e., 1,2-chlorohydroxylation), which is the most prominent access route to this class of compounds. Also, some other synthetic approaches involving the reduction of α-chloroketones, the epoxide opening ring by chloride anions and the utilisation of Grignard reagents for the synthesis of these compounds and chlorination of allylic alcohols are highlighted. Finally, enzymatic reactions for the formation of chlorohydrins are briefly summarised followed by a short view on natural products containing this moiety.

1 Introduction

2 Applications for the Synthesis of 1,2-Chlorohydrins

2.1 Chlorohydroxylation of Alkenes

2.2 Reduction of Chloroketones

2.3 Metalorganic Reagents

2.4 Epoxide Ring Opening

2.5 Chlorination of Allylic Alcohols

2.6 Biochemical Methods

2.7 Selected Applications in Natural Product Total Synthesis

3 Conclusion

Key words

alkene - addition - chlorohydrins - chloroketones - enzymatic reactions - epoxide ring opening - oxidation - reduction

Publication History

Received: 25 July 2022

Accepted: 21 September 2022

Article published online:
01 December 2022

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