You probably want to set sender_canonical_maps for outgoing mails. This way you get both header and envolope addresses rewritten.
But for incoming mails recipient_canonical_maps doesn't work since you can only map to one E-Mail address. Anyways it's probably cleaner to have recipient_bcc_maps (delivers to info, bob1 and bob2) or virtual_alias_maps (delivers to bob1 and bob2 instead of info).
So you should use something like this:
/etc/postfix/main.cf:
virtual_alias_maps = hash:/etc/postfix/virtual_alias_maps
sender_canonical_maps = hash:/etc/postfix/sender_canonical
/etc/postfix/sender_canonical:
bob1@domain.com info@domain.com
bob2@domain.com info@domain.com
/etc/postfix/virtual_alias_maps:
info@domain.com bob1@domain.com, bob2@domain.com
You maybe have to add domain.com in the virtual_alias_maps table if it is not already defined as one of Postfix destionation domains somewhere in your configuration.
Please have a look at Postfix' address rewriting README for more details.
PS: Your described behaviour sounds like an Issue Tracking System, so you may want to have a look at one of those systems: https://en.wikipedia.org/wiki/Comparison_of_issue-tracking_systems