The honour roll: Oyo Mitsunobu

Prior to 1967, people in the Haight-Ashbury neighborhood of San Francisco thought that they had seen it all. Little did they know that a social earthquake was about to befall them, which later became known as the Summer of Love. The music of Jefferson Airplane was in the air and I just wish I was around then, but I was not even conceived at that time. There is another memorable event that hails from that eventful year. Across the Pacific Ocean in Japan, the late Professor Oyo Mitsunobu (1934-2003) developed one of the most remarkable and useful reactions in the history of organic chemistry, the Mitsunobu process. There are a myriad of reasons to love this reaction, which epitomizes the so-called oxidation-reduction condensations. In the Mitsunobu reaction, the cost of installing a new bond comes from a combination of oxidation (phosphine into phosphine oxide) and reduction (DEAD into the corresponding hydrazine) processes. There are people who would say that this is not atom-economical, blah blah. No, it ain’t. But go tell this to Ed Grabowski, the retired process chemistry guru from Merck. He will tell you a thing or two about the immense utility of this “ungreen” reaction. I wish we had more ungreen processes like that, I tell you this much! Any chemistry that you use without worrying about referring to the original journal reference is in the lore of chemical synthesis. The Mitsunobu reaction is certainly there.


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