Issue 42, 2014

Introduction of prenyl fragment into chalcones through α-regioselective 1,2-addition in THF

Abstract

A practical and additive-free method for the prenylation of chalcones using prenylzinc is reported. The protocol described is attractive because it provides access to a new class of prenylated chalcone derivatives derived from two classes of natural products in a simple, high-yielding and regioselective synthetic step. Furthermore, the application of other allylic reagents in our new protocol is demonstrated. A plausible mechanism that invokes steric factors to account for the α-regioselective outcome is proposed.

Graphical abstract: Introduction of prenyl fragment into chalcones through α-regioselective 1,2-addition in THF

Supplementary files

Article information

Article type
Paper
Submitted
11 Apr 2014
Accepted
06 May 2014
First published
06 May 2014

RSC Adv., 2014,4, 21810-21814

Introduction of prenyl fragment into chalcones through α-regioselective 1,2-addition in THF

H. Jin, S. Zhang, R. Sun, F. Dou and L. Zhao, RSC Adv., 2014, 4, 21810 DOI: 10.1039/C4RA03301A

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