Highly stereoselective syn-ring opening of enantiopure epoxides with nitric oxide

Reaction of enantiopure epoxides (1) with NO occurred highly stereoselectively, affording syn-ring opened products, nitrates (2). The configuration of 2 was confirmed to be retained by determining the configuration of reduced products 1,2-glycols (4) from 2. A possible mechanism is suggested to trace out the syn-ring opening pathway.

Reaction of enantiopure epoxides (1) with NO afforded syn-ring opened products, nitrates (2). Their configurations were confirmed to be retained by determining the configuration of reduced products 1,2-glycols from 2.