text: Recent work has demonstrated that the scope of "soft" nucleophiles can be expanded to include some pronucleophiles that have much higher  than ~ 25. Some of these "soft" nucleophiles have  ranging all the way to 32, and even more basic pronucleophiles (~44) have been shown to act as soft nucleophiles with the addition of Lewis acids that help to facilitate deprotonation. The improved pKa range of "soft" nucleophiles is critical because these nucleophiles are the only ones that have been explored for enantioselective reactions until very recently (although non-enantioselective reactions of "hard" nucleophiles have been known for some time). By increasing the scope of pronucleophiles that act as "soft" nucleophiles, these substrates can also be incorporated into enantioselective reactions using previously reported and well characterized methods.