Alcohols from Alkenes through Hydroboration-Oxidation Anti-Markovnikov Syn Hydration

7 Alcohols from Alkenes through Hydroboration-Oxidation Anti-Markovnikov Syn Hydration 

The addition of water is indirect in this process, and two reactions are involved. The first is the addition of a boron atom and hydrogen atom to the double bond, called hydroboration the second is oxidation and hydrolysis of the alkylborane intermediate to an alcohol and boric acid. The anti-Markovnikov regiochenustry of the addition is illustrated by the hydroboration-oxidation of propene  

This can be seen in the following example with 1-methylcyclopentene  

In the following sections we shall consider details of the mechanism that lead to the anti-Markovnikov regiochemistry and syn stereochemistry of hydroboration-oxidation. 

Hydroboration of an aUcene is the starting point for a number of useful synthetic procedures, including the anti-Markovnikov syn hydration procedure we have just mentioned. Hydroboration was discovered by Herbert C. Brown (Purdue University), and it can be represented in its simplest terms as follows  

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ALCOHOLS FROM ALKENES THROUGH HYDROBORATION-OXIDATION ANTI-MARKOVNIKOV SYN HYDRATION... 

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