Re #1: Yes, I realize the strecker would be better for the first. However, I feel like this ought to work. Does anyone know if you can use reductive amination on a carboxylic acid? This seems to be the only potentially sticky point.
Re: #2: Wow, I did not notice the pentavalent carbon. Ironically, it was the professor who put that there, not me. Don't remember what I was thinking with that, I don't see how it could work in retrospect.