2020 Volume 32 Issue 187 Pages E87-E91
Glycosyl cations, which have been considered key intermediates for synthetic carbohydrate chemistry since the earliest days of the field, can sometimes act in unexpected and unpredictable ways. A close examination of these cations tells us that some of this behavior relies on well-tuned interactions that allow these cations to avoid undesired or unexpected reactions that would otherwise utilize these glycosyl cations aggressively. This minireview provides selected examples of how glycosyl cations can be “tamed” to favor desirable reactions, particularly for neighboring group participation and SN2-like reactions.
