If you start with a duplicate of a high resolution jpeg and attempt to apply the Markup Elliptical selection tool in Preview, when you click the crop button, it will warn you that the selection introduces transparency and do you want to overwrite the jpeg as a png? The resultant png is 300 dpi in my testing, just not jpeg as you preferred.
Here is a a crop result from an original JPEG image from a Leica Q2. I have chosen a black Preview window background. Note: this is a 72 dpi screen capture of the 5.6MB 300 DPI circular image (that the hosting software cannot post) cropped from Preview: