A fructose-based catalyst can be used for an asymmetric synthesis of these compounds in a reaction named for Shi.  
A fructose-based catalyst can be used for an asymmetric synthesis of these compounds in a reaction named for Shi.  The SqMO protein gives squalene this functionality in the rate limiting step of the sterol biosynthesis pathway. A titanium-based catalyst is used along with diethyl tartarate to synthesize these compounds in another reaction. Many syntheses of these compounds proceed via a spiro transition state. These compounds react with water to yield vicinal diols. Reacting alkenes with chlorine and water and then with a base yields this functionality via a halohydrin intermediate, and reacting alkenes with peroxyacids like MCPBA yields these compounds in a concerted reaction which proceeds via a "butterfly" mechanism. In the presence of an acid catalyst, they are readily catalyzed to glycols due to their high level of ring strain. For 10 points, name these compounds synthesized in the Sharpless reaction, cyclic ethers that are often used as adhesives. 
A fructose-based catalyst can be used for an asymmetric synthesis of these compounds in a reaction named for Shi.  
epoxides