Section 44.1

In response to a question as to whether shares issued from treasury of a corporation to a family trust, which later were distributed to a capital beneficiary, qualified as shares of an eligible small business corporation if they were shares of an active business corporation at their issuance and the $50 million test was satisfied, CRA found that a subsequent disposition of the shares by the beneficiary would not qualify as a qualifying disposition (TaxInterpretations translation):

One of the conditions is that requiring that a share be an "eligible small business corporation share" of the taxpayer.

In our view, the text of the definition of "qualifying disposition" and of "eligible small business corporation share" in subsection 44.1(1) requires that the common shares are issued to a taxpayer who qualifies for the purposes of a qualifying disposition. A trust is excluded from the definition of "qualifying disposition," which indicates that each of the shares described in your example cannot qualify as an "eligible small business corporation share" for purposes of subsection 44.1(1).