Sort by property in one-to-many association

I have the following scenario (Domain classes)

class Request { 
    String title                
    List statusUpdates

    static hasMany = [statusUpdates: StatusUpdate]
}

and

class StatusUpdate {

    Date dateCreated
    String statusFrom
    String statusTo
    String notes

    static belongsTo = Request
}

I am currently using createCriteria to implement filtering and basic sorting of Request.

Now I want to get a list of Requests starting from the most recently updated (ordered by the value of the field dateCreated of the last StatusUpdate for the Request)

Any hint?

assuming that every Request has at least one StatusUpdate and slightly changing belongsTo declaration, you could go the other direction:

class StatusUpdate {

    Date dateCreated
    String statusFrom
    String statusTo
    String notes

    static belongsTo = [req: Request] // I assume that naming the field "request" would cause whole bunch of weird problems, therefore "req"
}

StatusUpdate.createCriteria().list() {
    req {
        // your criteria for requests filtering
    }
    projections {
        groupProperty 'req', 'reqAlias'
        max 'dateCreated', 'maxDateCreatedAlias'
    }
    order 'maxDateCreatedAlias', 'desc'
}.collect { it[0] }