It always struck me that playing at 'a' looked like particularly bad shape when 'b' was available. It might be as simple as not making the empty triangle being a more efficient way to do the same thing (maintaining/increasing liberties for example).
My slightly more in depth undertanding of it is this, presuming some other stuff happens elsewhere on the board white might have the chance to play like this, black has to play 3 to separate the white groups and then comes under attack:
$$B
$$ | . . O . . . . . .
$$ | . . . X . . . . .
$$ | . . O X . 4 . . .
$$ | . . O X 1 O . X .
$$ | . . O O X 2 . . .
$$ | . . . . 3 . . . .
$$ +------------------
- Click Here To Show Diagram Code
[go]$$B
$$ | . . O . . . . . .
$$ | . . . X . . . . .
$$ | . . O X . 4 . . .
$$ | . . O X 1 O . X .
$$ | . . O O X 2 . . .
$$ | . . . . 3 . . . .
$$ +------------------[/go]
By comparison, if white tries to cut black in this variation, black's outside shape remains solid and white has to have significantly more support to attempt the cut. That's not to say it can't happen but it's harder for white to attack:
$$B
$$ | . . O . . . . . .
$$ | . . . X . . . . .
$$ | . . O X . . . . .
$$ | . . O X 2 O 3 X .
$$ | . . O O X 1 . . .
$$ | . . . . . . . . .
$$ +------------------
- Click Here To Show Diagram Code
[go]$$B
$$ | . . O . . . . . .
$$ | . . . X . . . . .
$$ | . . O X . . . . .
$$ | . . O X 2 O 3 X .
$$ | . . O O X 1 . . .
$$ | . . . . . . . . .
$$ +------------------[/go]
In addition, if black tenukis before connecting at all black can even sacrifice on the 2nd line to maintain good shape for relatively little gain on white's part:
$$W
$$ | . . O . . . . . .
$$ | . . . X . . 8 . .
$$ | . . O X . 6 . . .
$$ | . . O X 1 O 4 X .
$$ | . . O O X 2 3 . .
$$ | . . . . 7 5 . . .
$$ +------------------
- Click Here To Show Diagram Code
[go]$$W
$$ | . . O . . . . . .
$$ | . . . X . . 8 . .
$$ | . . O X . 6 . . .
$$ | . . O X 1 O 4 X .
$$ | . . O O X 2 3 . .
$$ | . . . . 7 5 . . .
$$ +------------------[/go]
Alternatively white could descend looking for fewer points but keeping holes in black's shape, but black could easily defend at a, b or c.
$$W
$$ | . . O . . . . . .
$$ | . . . X . a . . .
$$ | . . O X . b c . .
$$ | . . O X . O . X .
$$ | . . O O X 1 . . .
$$ | . . . . . . . . .
$$ +------------------
- Click Here To Show Diagram Code
[go]$$W
$$ | . . O . . . . . .
$$ | . . . X . a . . .
$$ | . . O X . b c . .
$$ | . . O X . O . X .
$$ | . . O O X 1 . . .
$$ | . . . . . . . . .
$$ +------------------[/go]
At this point if white playing to cut off the black stone on the 2nd line has become that good a move, either you have reached the early endgame (obviously it's still a huge move), or the black stones on the outside have already been neglected too much.
I think just looking at the shapes that arise from white attempting to cut through black in either variation it should be relatively obvious which is better locally. The only hesitation I have is that if black has come under heavy attack already it may be easier to defend like this if black had already connected solidly instead, starting to make eyeshape and getting out at a/b/c/d/e:
$$W
$$ | . . O . . e . . .
$$ | . . . X . . . d .
$$ | . . O X a 2 c . .
$$ | . . O X X O b X .
$$ | . . O O X 1 . . .
$$ | . . . . 3 . . . .
$$ +------------------
- Click Here To Show Diagram Code
[go]$$W
$$ | . . O . . e . . .
$$ | . . . X . . . d .
$$ | . . O X a 2 c . .
$$ | . . O X X O b X .
$$ | . . O O X 1 . . .
$$ | . . . . 3 . . . .
$$ +------------------[/go]
There may also be less aji in the corner for white when black doesn't connect solidly and likewise the 1st line endgame may end up being better for white, later on moves at 'a' or 'b' might be sente for white:
$$W
$$ | . . O . . . . . .
$$ | . . . X . . . . .
$$ | . . O X . . . . .
$$ | . . O X . O . X .
$$ | . . O O X X . . .
$$ | . . . a b . . . .
$$ +------------------
- Click Here To Show Diagram Code
[go]$$W
$$ | . . O . . . . . .
$$ | . . . X . . . . .
$$ | . . O X . . . . .
$$ | . . O X . O . X .
$$ | . . O O X X . . .
$$ | . . . a b . . . .
$$ +------------------[/go]
That's my two cents anyway! I think it's probably one of this instances where connecting underneath is locally better but it can also be highly situational