// MainPage.xaml.cs
using System.Collections.Generic;
using System.Windows.Controls;

namespace BindingListBoxToDictionary
{
    public partial class MainPage : UserControl
    {
        public MainPage()
        {
            InitializeComponent();
            this.DataContext = new Dictionary<string, bool> 
            {
                {"first", true},
                {"second", false},
                {"third", true},
                {"fourth", false},
            };
        }
    }
}

<!-- MainPage.xaml -->
<UserControl x:Class="BindingListBoxToDictionary.MainPage"
    xmlns="http://schemas.microsoft.com/winfx/2006/xaml/presentation"
    xmlns:x="http://schemas.microsoft.com/winfx/2006/xaml"
    xmlns:d="http://schemas.microsoft.com/expression/blend/2008"
    xmlns:mc="http://schemas.openxmlformats.org/markup-compatibility/2006"
    mc:Ignorable="d"
    d:DesignHeight="300" d:DesignWidth="400">
    <UserControl.Resources>
        <DataTemplate x:Key="DefaultDictionaryTemplate">
            <StackPanel Orientation="Horizontal">
                <TextBlock Text="{Binding Key}" />
                <TextBlock Text="{Binding Value}" />
            </StackPanel>
        </DataTemplate>
    </UserControl.Resources>
    <StackPanel Orientation="Vertical" x:Name="LayoutRoot" Background="White">
        <ListBox ItemsSource="{Binding}">
            <ListBox.ItemTemplate>
                <DataTemplate>
                    <CheckBox IsChecked="{Binding Value}" Content="{Binding Key}"/>
                </DataTemplate>
            </ListBox.ItemTemplate>
        </ListBox>
        <ListBox ItemsSource="{Binding}" ItemTemplate="{StaticResource DefaultDictionaryTemplate}"/>
    </StackPanel>
</UserControl>