In the presence of isolated ketones, can organocuprates add to secondary tosylates in an SN2 fashion without adding to the ketones?
1 Answer
Cuprates (also known as Gilman reagents) do not generally react with isolated ketones. If they did the widely used reaction of cuprates with alpha/beta unsaturated ketone would not work to give the substituted ketone product.
According to this review alkyl cuprates do react with secondary tosylates to give the expected SN2 product. I have not, however, been able to find an example of this being done in the presence of an isolated ketone