Issue 31, 2016
From the journal:

RSC Advances

Reverse regioselectivity in Pd(0)/InI-mediated allylation of aldehydes with ε-amido-allylindiums generated from β-lactams. A new entry to non-racemic highly substituted γ-butyrolactones†

Urszula Klimczak,a   Olga Staszewska-Krajewskaa  and  Bartosz K. Zambroń*a  

* Corresponding authors

a Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
E-mail: bartosz.zambron@icho.edu.pl

Abstract

ε-Amido-allylindiums generated from N-Ts-β-lactams in the presence of 2 eq. of InI, catalytic amounts of Pd(PPh3)4 and 5 eq. of CF3CO2H react regio- and stereoselectively with a number of aromatic and aliphatic aldehydes to afford γ-butyrolactones as the exclusive products in high yield.

Graphical abstract: Reverse regioselectivity in Pd(0)/InI-mediated allylation of aldehydes with ε-amido-allylindiums generated from β-lactams. A new entry to non-racemic highly substituted γ-butyrolactones

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Article information

DOI
https://doi.org/10.1039/C6RA00517A
Article type
Paper
Submitted
07 Jan 2016
Accepted
29 Feb 2016
First published
02 Mar 2016

RSC Adv., 2016,6, 26451-26460

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Reverse regioselectivity in Pd(0)/InI-mediated allylation of aldehydes with ε-amido-allylindiums generated from β-lactams. A new entry to non-racemic highly substituted γ-butyrolactones

U. Klimczak, O. Staszewska-Krajewska and B. K. Zambroń, RSC Adv., 2016, 6, 26451 DOI: 10.1039/C6RA00517A

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