What I'm about to provide is an intimidating list, but the only thing that's
really critical to read prior to
A Singular Destiny is the
Destiny trilogy, for much the same reason that "Family" works much better if you've watched "The Best of Both Worlds" before it. OTOH, "Family" works even better if you've been following Wesley's travails and the ongoing Klingon stuff with Worf.
Having said that, I wrote
ASD to be as accessible as possible without having read bupkuss beforehand. I have no idea if I succeeded -- I'll leave that to finer minds than mine -- but I did try.
Anyhow, here's an annotated list, so you can prioritize:
Pre-Nemesis
There was a nine-book series that set the groundwork for
Nemesis as well as many of the post-
Nemesis books. None of them are critical. All nine provide some nice background, particularly on Christine Vale, the security chief on the
Enterprise-E who goes on to become Riker's first officer on
Titan, and the final five books set up Riker's captaincy and engagement to Troi (both established in
Nemesis), as well as the political situation we see going forward. It's also, in essence, Data's final arc, which runs through all nine.
These books take place from late 2378 to late 2379 (the film took place in late 2379).
A Time to be Born by John Vornholt
A Time to Die by John Vornholt
A Time to Sow by Dayton Ward & Kevin Dilmore
A Time to Harvest by Dayton Ward & Kevin Dilmore
A Time to Love by Robert Greenberger
A Time to Hate by Robert Greenberger
A Time to Kill by David Mack
A Time to Heal by David Mack
A Time for War, a Time for Peace by Keith R.A. DeCandido
Post-Nemesis
Here's where we get to the nitty gritty.
The
Titan books pick up with Riker, Troi, and a bunch of other folks on the good ship
Titan, starting with the mission to Romulus mentioned in
Nemesis (the first two books, which also sets up the civil unrest that grows out of Shinzon's failed coup in the movie), and then continuing through to their deep-space exploration mission (the next two).
Taking Wing by Michael A. Martin & Andy Mangels
The Red King by Andy Mangels & Michael A. Martin
Orion's Hounds by Christopher L. Bennett
Sword of Damocles by Geoffrey Thorne
Meanwhile, the adventures of the
Enterprise-E do continue. We get some changes in the relationships of some of the main characters (Friedman), plus setting up the Borg storyline (Dillard, David, Bennett), and establishing several new characters (Dillard, DeCandido, Bennett) to replace Riker, Troi, and Data.
Death in Winter by Michael Jan Friedman
Resistance by J.M. Dillard
Q & A by Keith R.A. DeCandido
Before Dishonor by Peter David
Greater than the Sum by Christopher L. Bennett
The political end of things is also covered in an off-the-beaten-path novel that covers the year or so following
Nemesis from the point of view of the Federation government. This is President Nan Bacco's first year in office -- the character was introduced in
A Time for War, a Time for Peace, and plays a supporting role in
Destiny -- and (among other things) does more with the ongoing Romulan
mishegoss:
Articles of the Federation by Keith R.A. DeCandido
The above-listed books all take place in 2380 (roughly speaking), with
Articles covering the entire year.
Destiny
We come into 2381 here, and it all comes together in this big-ass trilogy, and then my followup:
Destiny: Gods of Night by David Mack
Destiny: Mere Mortals by David Mack
Destiny: Lost Souls by David Mack
A Singular Destiny by Keith R.A. DeCandido
Again, let me stress: you can jump right in and read
ASD on its own, and you can jump right into
Destiny.
Two people have already cross-posted ahead of me, but I wanted to make sure I was comprehensive.